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Total synthesis of (+)-sorangicin A.

ABSTRACT: The final synthetic challenges associated with (+)-sorangicin A have been overcome, thus leading to the first total synthesis of this complex macrolide antibiotic. Highlights of the highly convergent synthesis include two Julia-Kociénski olefinations to unite three advanced fragments with high E-stereoselectivity. Critical to the final-stage success was the use of a carefully defined Stille coupling and a Mukaiyama macrolactonization as well as Lewis and protic acid-promoted deprotections carefully designed to suppress E/Z isomerization and/or destruction of the delicate (Z,Z,E)-trienoate linkage.

SUBMITTER: Smith AB

PROVIDER: S-EPMC2749982 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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Total synthesis of (+)-sorangicin A.

Smith Amos B AB Dong Shuzhi S Brenneman Jehrod B JB Fox Richard J RJ

Journal of the American Chemical Society 20090901 34

The final synthetic challenges associated with (+)-sorangicin A have been overcome, thus leading to the first total synthesis of this complex macrolide antibiotic. Highlights of the highly convergent synthesis include two Julia-Kociénski olefinations to unite three advanced fragments with high E-stereoselectivity. Critical to the final-stage success was the use of a carefully defined Stille coupling and a Mukaiyama macrolactonization as well as Lewis and protic acid-promoted deprotections carefu ...[more]

PMID: 19663510

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