Total Synthesis of (+)-SCH 351448

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 esterifica...

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Bibliographic Details
Published in:Organic letters 2011-09, Vol.13 (17), p.4652-4655
Main Authors: Zhu, Kaicheng, Panek, James S
Format: Article
Language:English
Subjects:
Lactones - chemical synthesis
Lactones - chemistry
Molecular Conformation
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol201863b