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An expeditious total synthesis of both diastereoisomeric lipid dihydroxytetrahydrofurans from Notheia anomala.

ABSTRACT: Short, high yielding syntheses of both diastereomers of the naturally occurring oxylipids 1 and 2 using a combination of organocatalytic hydroxylation of an aldehyde, alkene cross metathesis, and palladium(0) catalyzed cyclization chemistry (six-step process) are reported. Furthermore, the influence of the catalyst on the cross metathesis reaction of the homoallylic 1,2-diol has been studied in detail.

SUBMITTER: Roy S

PROVIDER: S-EPMC3345562 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

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An expeditious total synthesis of both diastereoisomeric lipid dihydroxytetrahydrofurans from Notheia anomala.

Roy Sudeshna S Spilling Christopher D CD

Organic letters 20120416 9

Short, high yielding syntheses of both diastereomers of the naturally occurring oxylipids 1 and 2 using a combination of organocatalytic hydroxylation of an aldehyde, alkene cross metathesis, and palladium(0) catalyzed cyclization chemistry (six-step process) are reported. Furthermore, the influence of the catalyst on the cross metathesis reaction of the homoallylic 1,2-diol has been studied in detail. ...[more]

PMID: 22506757

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