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Short, enantioselective total synthesis of chatancin.


ABSTRACT: An enantioselective total synthesis of the polycyclic diterpene (+)-chatancin, a potent PAF antagonist, is reported. Proceeding in seven steps from dihydrofarnesal, this synthetic route was designed to circumvent macrocyclization-based strategies to complex, cyclized cembranoids. The described synthesis requires only six chromatographic purifications, is high yielding, and avoids protecting-group manipulations. An X-ray crystal structure of this fragile marine natural product was obtained.

SUBMITTER: Zhao YM 

PROVIDER: S-EPMC4300267 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature

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Short, enantioselective total synthesis of chatancin.

Zhao Yu-Ming YM   Maimone Thomas J TJ  

Angewandte Chemie (International ed. in English) 20141202 4


An enantioselective total synthesis of the polycyclic diterpene (+)-chatancin, a potent PAF antagonist, is reported. Proceeding in seven steps from dihydrofarnesal, this synthetic route was designed to circumvent macrocyclization-based strategies to complex, cyclized cembranoids. The described synthesis requires only six chromatographic purifications, is high yielding, and avoids protecting-group manipulations. An X-ray crystal structure of this fragile marine natural product was obtained. ...[more]

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