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Application of tandem ring-closing enyne metathesis: formal total synthesis of (-)-cochleamycin A.

ABSTRACT: A tandem ring-closing metathesis of a silaketal-based dienyne substrate proceeded efficiently to provide a bicyclic siloxane, which upon removal of the silicon tether afforded an (E,Z)-1,3-dienediol. Further manipulation of this key functional motif rendered synthesis of the entire C1-C19 linear skeleton of (-)-cochleamycin A, a late-stage intermediate employed in the previous total synthesis of (+)-cochleamycin A by Roush and co-workers.

SUBMITTER: Mukherjee S

PROVIDER: S-EPMC2715010 | biostudies-literature | 2009 Jul

REPOSITORIES: biostudies-literature

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Application of tandem ring-closing enyne metathesis: formal total synthesis of (-)-cochleamycin A.

Mukherjee Sumit S Lee Daesung D

Organic letters 20090701 13

A tandem ring-closing metathesis of a silaketal-based dienyne substrate proceeded efficiently to provide a bicyclic siloxane, which upon removal of the silicon tether afforded an (E,Z)-1,3-dienediol. Further manipulation of this key functional motif rendered synthesis of the entire C1-C19 linear skeleton of (-)-cochleamycin A, a late-stage intermediate employed in the previous total synthesis of (+)-cochleamycin A by Roush and co-workers. ...[more]

PMID: 19507873

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