The total synthesis of (.+-.)-patulolide A.

Makita, Atsushi; Yamada, Yasuhiro; Okada, Hirosuke

doi:10.7164/antibiotics.39.1257

Cited by 22 publications

(9 citation statements)

References 18 publications

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“…Synthesis of (+)-Patulolide A. Since (+)-patulolide A is synthesized from acid 41 by macrolactonization followed by deprotection, 14b,d we planned a synthesis of acid 41 as shown in Scheme 3, where the key intermediate is the furan 38 . Alkylation of 1-bromo-5-chloropentane with 2-furyllithium ( 33 ) afforded the chloride 34 in 95% yield according to the procedure of Büchi .…”

Section: Resultsmentioning

confidence: 99%

“…Slightly acidic conditions (pH 5−6) and short reaction times (4 h) coupled with easy handling seem to suit the present purpose. Thus, to test the generality of this key oxidation and efficiency of the overall furan-methodology, we have carried out the asymmetric syntheses of (+)-aspicilin, (+)-patulolide A, 3f, and (−)-pyrenophorin. ,10c,14e, Herein we describe full results of our experimentation …”

Section: Introductionmentioning

confidence: 99%

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Efficient Conditions for Conversion of 2-Substituted Furans into 4-Oxygenated 2-Enoic Acids and Its Application to Synthesis of (+)-Aspicilin, (+)-Patulolide A, and (−)-Pyrenophorin

et al. 1998

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2-Substituted furans 1a,b,c were found to be conveniently transformed into trans 4-oxo-2-enals 2a,b,c in 62-87% yields by using NBS/pyridine in THF-acetone-H(2)O (<-15 degrees C then rt) or NBS/NaHCO(3) in acetone-H(2)O (<-15 degrees C then rt after addition of pyridine). Further oxidation of the enals 2a-c using NaClO(2) led to the trans 4-oxo-2-enoic acids 3a-c in good yields. With this transformation in mind, we designed syntheses of (+)-aspicilin, (+)-patulolide, and (-)-pyrenophorin. In the synthesis of (+)-aspicilin as shown in Schemes 1 and 2, the pivotal intermediate 6 was prepared from olefin 7 in which 2-furyl group is attached. The AD reaction of 7 secured the C(5) and C(6) stereochemistry of aspicilin, and the subsequent transformation using the protocol described above afforded the ester 6. Stereocontrolled reduction of 6 followed by deprotection and the Yamaguchi macrocyclization furnished (+)-aspicilin. For the synthesis of (+)-patulolide (Scheme 3) and (-)-pyrenophorin (Scheme 4), the intermediates are the furans 38 and 44, which were prepared easily by the classical methods using furyllithium 33. The furan ring oxidations proceeded as well, furnishing acids 40 and 46 in good yields, acetalization of which afforded the known intermediates 41 and 47, respectively.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Efficient Conditions for Conversion of 2-Substituted Furans into 4-Oxygenated 2-Enoic Acids and Its Application to Synthesis of (+)-Aspicilin, (+)-Patulolide A, and (−)-Pyrenophorin

et al. 1998

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“…Synthesis of (+)-Patulolide-C (1) began with the coupling of enone (10) with sulfone (22) under Julia olefination condition [18] to afford corresponding diene (11) as an mixture of E/Z isomers with 12.6 : 1 ratio. Diene (11) was then subjected to catalytic hydrogenation using Pd(OH) 2 [18d] to afford saturated compound 12.The latter upon treatment with either pTSA/MeOH or methanolic HCl yield triol (13) as shown in Scheme 5. Several attempts targeted at the selective deprotection of acetonide of 12 in presence of TBDMS ether were unsuccessful [19] and resulted in a mixture of products.…”

Section: Resultsmentioning

confidence: 99%

“…[1] The compounds were isolated from Peniciliumurticae S11R59 and characterized by Yamada and co-workers . [1,2] Its seco-acid 17 is characterized by the presence of stereogenic centers at 4and 11-positions. Total synthesis of structurally related Patulolide has been reported in the literature.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of (+)‐Patulolide C Using R‐(+)‐γ‐Valerolactone as a Chiral Synthon.

et al. 2017

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The total synthesis of (+)‐Patulolide‐C is accomplished by using enantiopure R‐(+)‐γ‐valerolactone & R‐(+)‐epichlorohydrin as chiral synthons. The strategy adopted for the synthesis is a convergent approach wherein two advanced intermediates were synthesized independently using the chiral synthons and coupled to achieve the skeleton of Patulolide‐C. The important synthetic steps of the synthesis are two carbon homologation of the cyclic lactol, Julia olefination of enone with sulfone in DME, DIBAl‐H mediated regioselective opening of benzylidine acetal, selective oxidation of primary alcohol to aldehyde using BAIB/TEMPO and lactonization of seco‐acid adopting Yamaguchi protocol to afford the macrolide skeleton.

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“…Patulolide A (Figure ) is a 12‐member macrolide, and it was isolated from Penicillium urticae S11R59 by Yamada and his coworkers . Patulolide A showed antifungal, antibacterial, and anti‐inflammatory activities . Moreover, Patulolide A inhibits the IgE‐induced release of histamine for human leucocytes better than the degeneration inhibitor, theophylin …”

Section: Introductionmentioning

confidence: 99%