Stereoselective total synthesis of (+)-cardiobutanolide and (+)-3-epi-cardiobutanolide from diacetone d-glucose

Krishna, Palakodety Radha; Reddy, P. Vishnuvardhan

doi:10.1016/j.tetlet.2006.04.146

Cited by 17 publications

(5 citation statements)

References 30 publications

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“…These pertain to the synthesis of (i) pregnanone derivatives, (ii) glucosphingolipids, (iii) pyrrolidine-amide oligonucleotide mimics, (iv) tubronic acid, (v) enantiopure butanoates, (vi) macroviracins, (vii) reduced products of cis - and trans -hexahydronaphthalenones, (viii) stereoinversion of myo -inositol into scyllo -inositol, (ix) orthogonally-protected and unprotected depsipeptides such as l -Lys- d -Ala- d -Lac and Boc-( S )-HOMeVal-( R )-Hmb, (x) (2 S ,3 S ,4 R )-4-( tert -butyldimethylsilyloxy)-2,3-isopropylidenedioxy-4-phenylbutanoate, (xi) dihydroxycholesterol, (xii) the acetate of the triol derived from jasminine, (xiii) stereochemically inverted products of xylofuranosyl derivatives, (xiv) 6- epi- aucubin, (xv) hydroxyethylene dipeptide isosteres (e.g. L-682,679), (xvi) orobanchol (a germination stimulant), (xvii) long chain pentadeca-1,3,5,7,9,11,13,15-octols (16 diastereomers), (xviii) mycalamide A (natural product), (xix) murisolin (natural product), (xx) leucascandrolide A (natural product with a sterically congested carbon), , (xxi) l -lyxose esters, (xxii) cryptophycin (5-hydroxy acid subunit), (xxiii) polycyclic carbohydrates, (xxiv) protected aminooxyprolines, (xxv) carbahexopyranose stereoisomers, (xxvi) deoxynucleic guanidine (DNG) oligonucleotide, (xxvii) D-hica, a component of kulokekahilide-2, (xxviii) methylsulfonate esters, (xxix) (4 R ,5 S )- and (4 S ,5 R )-muricatacins, (xxx) trioxilins, (xxxi) functionalized β-C-glycosyl aldehydes (a part of ambruticin), (xxxii) pyrrolidinols, (xxxiii) carbocyclic nucleosides, (xxxiv) Δ 2 -OPC-8:0 (a substituted cyclopentanone derivative), (xxxv) fluorescence-labeled probes based on phyllanthurinolactone [in these cases, 4-dimethylaminophenyldiphenylphosphine ( 2 ) instead of Ph 3 P worked better], (xxxvi) (+)-cardiobutanolide, (xxxvii) 3-amino-2,3,6-trideoxysugars, (xxxviii) sesquiterpene lactones, (xxxix) 3-methylcyclopentadecanol, (xl) optically active β-methyl-γ-alkyl-γ-butyrolactone, (xli) chiral P,N-ligands with a cyclohexane backbone, (xlii) optically active aminobenzindanol, (xliii) cyclopenta[ d ]pyridazinediol, (xliv) 4-hydroxytetrahydropyranone, (xlv) alkynic esters as precursors to chiral substituted phthalides, (xlvi) tetracyclic lactones as structural analogues of kaurane diterpenoids, (xlvii) pyrrolidine- trans -lactones,...…”

Section: Carboxylic Acids/phosphorus-based Acids As Nucleophiles: Est...mentioning

confidence: 99%

Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

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His research interests include Organophosphorus Chemistry and Main Group Chemistry. He has over 115 publications so far and is a fellow of the Indian Academy of Sciences, Bangalore. N. N. Bhuvan Kumar was born in Cherukupalli, Guntur, India. After completing his B.Sc. from Nagarjuna University, he joined the School of Chemistry, University of Hyderabad, as a postgraduate student in the year 2000 and obtained his Master's degree in Chemistry. Currently, he is pursuing a Ph.D. on Organophosphonates under the supervision of Prof. K. C. Kumara Swamy. E. Balaraman was born in Kancheepuram, Chennai, India, in 1980. He received his M.Sc. in Chemistry from Vivekananda College [Madras University (2002)] and his Ph.D. degree in the areas of organophosphonates and modified BINOLs under the guidance of Prof. K. C. Kumara Swamy. Presently he is a postdoctoral fellow with Professors David Milstein and Ronny Neumann at the Weizmann Institute of Science, Israel. K. V. P. Pavan Kumar was born in Hyderabad (Andhra Pradesh), India, in 1979. He obtained his B.Sc. (Chemistry Honors) and M.Sc. (Chemistry) degrees from Sri Sathya Sai Institute of Higher Learning, Puttaparthi, A.P., India. He obtained his Ph.D. degree under the guidance of Prof. K. C. Kumara Swamy in October 2006. Presently he is working as a postdoctoral fellow in the area of hydroamination reactions using new titanium catalysts with Prof. Pierre Le Gendre at the Universite ´de Bourgogne, France.

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Section: Carboxylic Acids/phosphorus-based Acids As Nucleophiles: Est...mentioning

confidence: 99%

Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

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“…There are three classic methods to make the configuration inversion on secondary hydroxy groups: the first of them is the traditional method of oxidation-reduction, 19 in which a hydroxy group is oxidized in a first stage to a ketonic carbonyl group, for in the following stage to be stereoselectively reduced by hydride, to give in the end a hydroxy group with opposite stereochemistry to that of initial secondary alcohol. The inversion of configuration of secondary hydroxy groups can also be made through Mitsunobu's reaction, 20 in which occurs the activation of hydroxy group in a first stage by formation of an alkoxyphosphonium, for soon afterwards to occur the nucleophylic displacement of this activated leaving group. In the last case, we can cite the method of hydroxy activation by formation of correspondent mesylate, in which the inversion of configuration occurs by nucleophylic displacement of mesylate leaving group.…”

Section: Reactions Of the Lactonic Fusion Inversion On Eremanthine Dementioning

confidence: 99%

Study of the inversion reaction of the lactonic fusion on eremanthine derivatives

Alves¹,

Fantini²

2007

J. Braz. Chem. Soc.

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As α-metileno-γ-lactonas 4(15)-diidroeremantina (8), 4(15),9(10)-tetraidroeremantina (9), isoeremantina (10), acetato alílico Δ 1,10 (11), 1(R),10(R)-diidromiqueliolido (12) e 4α-hidróxi acetato alílico Δ 1,10 (13) foram sintetizadas a partir do produto natural abundante eremantina (1). Essas substâncias foram submetidas à reação de hidrólise com KOH aquoso e os sais carboxílicos dessas lactonas tiveram suas hidroxilas ativadas na posição C-6, pela formação dos respectivos mesilatos (MsCl, Et 3 N, THF ou DMSO) para deslocamento nucleofílico efetuado pelo grupo carboxilato. A utilidade dessa metodologia foi investigada para a obtenção de guaianolidos com fusão lactônica cis na posição C6-C7 e para sintetizar um precursor para estudo posterior da transformação biomimética de guaianolidos em pseudoguaianolidos.The α-methylene-γ-lactones 4(15)-dihydroeremanthine (8), 4(15),9(10)-tetrahydroeremanthine (9), isoeremanthine (10), allylic acetate Δ 1,10 (11), 1(R),10(R)-dihydromicheliolide (12) and 4α-hydroxy allylic acetate Δ 1,10 (13) were synthesized from the abundant natural product eremanthine (1). These substances were submitted to hydrolysis reaction with aqueous KOH and the carboxylic salts of these lactones had their hydroxy groups activated at the C-6 position by formation of respective mesylates (MsCl, Et 3 N, THF or DMSO) which underwent further displacement by carboxylate group. The utility of this methodology was investigated in order to obtain guaianolides with cis lactonic fusion at the C6-C7 position and to synthesize a precursor for posterior study of the biomimetic transformation of guaianolides into pseudoguaianolides.

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“…The synthesis by Yoda and Co‐workers used D ‐glucuronolactone and involves a long synthetic route (9 % overall yield) 6b. A synthesis from D ‐glucose derivative was reported by Krishna et al 6c. in 8 % overall yield.…”

Section: Introductionmentioning

confidence: 99%