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Direct entry to erythronolides via a cyclic bis[allene].

ABSTRACT: The complexity and low tractability of antibiotic macrolides pose serious challenges to addressing the problem of resistance through semi- or total synthesis. Here we describe a new strategy involving the preparation of a complex yet tractable macrocycle and the transformation of this macrocycle into a range of erythronolide congeners. These compounds represent valuable sectors of erythromycinoid structure space and constitute intermediates with the potential to provide further purchase in this space. The routes are short. The erythronolides were prepared in three or fewer steps from the macrocycle, which was prepared in a longest linear sequence of 11 steps.

SUBMITTER: Liu K

PROVIDER: S-EPMC3235949 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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Direct entry to erythronolides via a cyclic bis[allene].

Liu Kai K Kim Hiyun H Ghosh Partha P Akhmedov Novruz G NG Williams Lawrence J LJ

Journal of the American Chemical Society 20110906 38

The complexity and low tractability of antibiotic macrolides pose serious challenges to addressing the problem of resistance through semi- or total synthesis. Here we describe a new strategy involving the preparation of a complex yet tractable macrocycle and the transformation of this macrocycle into a range of erythronolide congeners. These compounds represent valuable sectors of erythromycinoid structure space and constitute intermediates with the potential to provide further purchase in this ...[more]

PMID: 21894913

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