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Total synthesis of (+)-SCH 351448.

ABSTRACT: A convergent synthesis of (+)-SCH 351448 (1), a monosodium salt of a C(2)-symmetric macrodiolide, is described. Our approach is based on a [4 + 2] annulation with a chiral allyl silane (anti-5c) to assemble the pyran subunits. Homodimerization was carried out in a stepwise fashion; initial esterification at C29' followed by macrocyclization at C29 afforded the desired macrodiolide.

SUBMITTER: Zhu K

PROVIDER: S-EPMC3164292 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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Total synthesis of (+)-SCH 351448.

Zhu Kaicheng K Panek James S JS

Organic letters 20110811 17

A convergent synthesis of (+)-SCH 351448 (1), a monosodium salt of a C(2)-symmetric macrodiolide, is described. Our approach is based on a [4 + 2] annulation with a chiral allyl silane (anti-5c) to assemble the pyran subunits. Homodimerization was carried out in a stepwise fashion; initial esterification at C29' followed by macrocyclization at C29 afforded the desired macrodiolide. ...[more]

PMID: 21834568

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