Stereoselective Synthesis of (+)-Goniothalesdiol

Prasad, Kavirayani R.; Gholap, Shivajirao L.

doi:10.1021/jo060159f

Cited by 39 publications

(30 citation statements)

References 16 publications

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“…Synthesis of 36 from 16 was accomplished by us, earlier in our work concerning the total synthesis of related natural product goniothalesdiol. 13 Thus, alcohol 16 was converted to the tetrahydrofuran 36 by using the procedure described by us. 13 Ozonolysis of 36 furnished the corresponding lactol, which on subsequent oxidation with Ag 2 CO 3 impregnated on Celite afforded dihydroaltholactone 37 in 82% yield.…”

Section: Resultsmentioning

confidence: 99%

Stereoselective Total Synthesis of Bioactive Styryllactones (+)-Goniofufurone, (+)7-epi-Goniofufurone, (+)-Goniopypyrone, (+)-Goniotriol, (+)-Altholactone, and (−)-Etharvensin

Prasad

Gholap

2007

J. Org. Chem.

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Stereoselective total synthesis of biologically active styryllactones 7-epi-goniofufurone, goniofufurone, goniopypyrone, goniotriol, altholactone, and etharvensin was achieved in high overall yields from a common intermediate derived from d-(-)-tartaric acid. It is based on the utility of a masked tetrol, comprising an alkene tether and four contiguous hydroxy groups. The pivotal reaction sequence involves hydroxy-directed lactonization via the oxidation of alkene, and subsequent elaboration to styryllactones. The masked tetrol was prepared by the extension of gamma-phenyl-gamma-hydroxy butyramide, readily obtained from the bis-dimethylamide of tartaric acid, employing a combination of selective Grignard additions and a stereoselective reduction.

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Section: Resultsmentioning

confidence: 99%

Stereoselective Total Synthesis of Bioactive Styryllactones (+)-Goniofufurone, (+)7-epi-Goniofufurone, (+)-Goniopypyrone, (+)-Goniotriol, (+)-Altholactone, and (−)-Etharvensin

Prasad

Gholap

2007

J. Org. Chem.

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“…Whereas no improvements were noted for the thymine, uracil and 5F-uracil cases (entries 2, 4 and 8), significantly higher yields were noted with adenine (entry 6, 60% yield), along with cytosine and its derivative (entries 10 and 12). The role of the Lewis acid in these reactions has yet to be elucidated, but its acidic character could allow for complexation to the sulfonate oxygens of the C4′ protecting group, enhancing its leaving group ability …”

Section: Resultsmentioning

confidence: 99%

A Stereoselective Approach to β-l-Arabino Nucleoside Analogues: Synthesis and Cyclization of Acyclic 1′,2′-synN,O-Acetals

2012

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Reported herein is a novel and versatile strategy for the stereoselective synthesis of unnatural β-L-arabinofuranosyl nucleoside analogues from acyclic N,OTMS-acetals bearing pyrimidine and purine bases. These unusual acetals undergo a C1' to C4' cyclization where the OTMS of the acetal serves as the nucleophile to generate 2'-oxynucleosides with complete retention of configuration at the C1' acetal center. N,OTMS-acetals are obtained diastereoselectively from additions of silylated nucleobases onto acyclic polyalkoxyaldehydes in the presence of MgBr(2)·OEt(2). The strategy reported is addressing important synthetic challenges by providing stereoselective access to unnatural L-nucleosides starting from easily accessible pools of D-sugars and, as importantly, by allowing the formation of the sterically challenging 1',2'-cis nucleosides. A wide variety of nucleoside analogues were synthesized in 7-8 steps from easily accessible D-xylose.

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“…The synthetic sequence commenced with the addition of 1.5 equiv of n -heptylmagnesium bromide to diamide 6 and afforded the γ-oxo-amide 7 in 73% yield (Scheme ) . Reduction of the keto group in 7 with NaBH 4 /CeCl 3 gave a nonseparable diastereomeric mixture of alcohols in a 95:5 ratio, 5 being the major diastereomer in 90% yield.…”

Section: Resultsmentioning

confidence: 99%

Enantioselective Synthesis of Possible Diastereomers of Heptadeca-1-ene-4,6-diyne-3,8,9,10-tetrol; Putative Structure of a Conjugated Diyne Natural Product Isolated from Hydrocotyle leucocephala

Prasad

Swain

2011

J. Org. Chem.

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Enantioselective synthesis of possible diastereomers of heptadeca-1-ene-4,6-diyne-3,8,9,10-tetrol, a structure proposed for the natural product isolated from Hydrocotyle leucocephala is accomplished. The reported spectral data of the natural product did not match those of any of the isomers that were synthesized and established that the structure proposed for the natural product is not correct and requires revision.

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Stereoselective Synthesis of (+)-Goniothalesdiol

Cited by 39 publications

References 16 publications

Stereoselective Total Synthesis of Bioactive Styryllactones (+)-Goniofufurone, (+)7-epi-Goniofufurone, (+)-Goniopypyrone, (+)-Goniotriol, (+)-Altholactone, and (−)-Etharvensin

Stereoselective Total Synthesis of Bioactive Styryllactones (+)-Goniofufurone, (+)7-epi-Goniofufurone, (+)-Goniopypyrone, (+)-Goniotriol, (+)-Altholactone, and (−)-Etharvensin

A Stereoselective Approach to β-l-Arabino Nucleoside Analogues: Synthesis and Cyclization of Acyclic 1′,2′-synN,O-Acetals

Enantioselective Synthesis of Possible Diastereomers of Heptadeca-1-ene-4,6-diyne-3,8,9,10-tetrol; Putative Structure of a Conjugated Diyne Natural Product Isolated from Hydrocotyle leucocephala

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