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An efficient, modular approach for the synthesis of (+)-strictifolione and a related natural product.

ABSTRACT: An efficient, library amenable, "pot economical" total synthesis of (+)-strictifolione and the related natural product, (6R)-6[(E,4R,6R)-4,6-dihydroxy-10-phenyl-1-decenyl]-5,6-dihydro-2H-2-pyrone, are reported. This modular approach takes advantage of two consecutive phosphate tether-mediated, one-pot, sequential protocols, followed by a final cross metathesis to deliver both antifungal natural products in a three-pot process from the respective enantiomeric (R,R)- and (S,S)-trienes with minimal purification. A salient feature of this route is that additional protecting groups are not required as a result of the orthogonal protecting- and leaving-group properties innate to phosphate triesters.

SUBMITTER: Jayasinghe S

PROVIDER: S-EPMC4179430 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature

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An efficient, modular approach for the synthesis of (+)-strictifolione and a related natural product.

Jayasinghe Susanthi S Venukadasula Phanindra K M PK Hanson Paul R PR

Organic letters 20131202 1

An efficient, library amenable, "pot economical" total synthesis of (+)-strictifolione and the related natural product, (6R)-6[(E,4R,6R)-4,6-dihydroxy-10-phenyl-1-decenyl]-5,6-dihydro-2H-2-pyrone, are reported. This modular approach takes advantage of two consecutive phosphate tether-mediated, one-pot, sequential protocols, followed by a final cross metathesis to deliver both antifungal natural products in a three-pot process from the respective enantiomeric (R,R)- and (S,S)-trienes with minimal ...[more]

PMID: 24294936

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