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Phosphate tether-mediated approach to the formal total synthesis of (-)-salicylihalamides A and B.

ABSTRACT: A concise formal synthesis of the cytotoxic macrolides (-)-salicylihalamides A and B is reported. Key features of the synthetic strategy include a chemoselective hydroboration, highly regio- and diastereoselective methyl cuprate addition, Pd-catalyzed formate reduction, and an E-selective ring-closing metathesis to construct the 12-membered macrocycle subunit. Overall, two routes have been developed from a readily prepared bicyclic phosphate (4 steps), a 13-step route and a more efficient 9-step sequence relying on regioselective esterification of a key diol.

SUBMITTER: Chegondi R

PROVIDER: S-EPMC3271935 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature

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Phosphate tether-mediated approach to the formal total synthesis of (-)-salicylihalamides A and B.

Chegondi Rambabu R Tan Mary M L MM Hanson Paul R PR

The Journal of organic chemistry 20110419 10

A concise formal synthesis of the cytotoxic macrolides (-)-salicylihalamides A and B is reported. Key features of the synthetic strategy include a chemoselective hydroboration, highly regio- and diastereoselective methyl cuprate addition, Pd-catalyzed formate reduction, and an E-selective ring-closing metathesis to construct the 12-membered macrocycle subunit. Overall, two routes have been developed from a readily prepared bicyclic phosphate (4 steps), a 13-step route and a more efficient 9-step ...[more]

PMID: 21504150

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