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Total synthesis of dolabelide C: a phosphate-mediated approach.

ABSTRACT: The first synthesis of dolabelide C (1), a cytotoxic marine macrolide, is reported utilizing a phosphate tether-mediated approach. Bicyclic phosphates (S,S,S(P))-5 and (R,R,R(P))-5 serve as the central building blocks for the construction of two major 1,3-anti-diol subunits in 1 through selective cleavage pathways, regioselective olefin reduction, and cross-metathesis. Overall, phosphate-mediated processes provided copious amounts of both major subunits allowing for a detailed RCM macrocyclization study to the 24-membered macrolactone 1.

SUBMITTER: Hanson PR

PROVIDER: S-EPMC3150593 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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Total synthesis of dolabelide C: a phosphate-mediated approach.

Hanson Paul R PR Chegondi Rambabu R Nguyen John J Thomas Christopher D CD Waetzig Joshua D JD Whitehead Alan A

The Journal of organic chemistry 20110429 11

The first synthesis of dolabelide C (1), a cytotoxic marine macrolide, is reported utilizing a phosphate tether-mediated approach. Bicyclic phosphates (S,S,S(P))-5 and (R,R,R(P))-5 serve as the central building blocks for the construction of two major 1,3-anti-diol subunits in 1 through selective cleavage pathways, regioselective olefin reduction, and cross-metathesis. Overall, phosphate-mediated processes provided copious amounts of both major subunits allowing for a detailed RCM macrocyclizati ...[more]

PMID: 21528846

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