Stereoselectivity of model C22-23 aldol coupling for spirangiens A & B

Claire Gregg, Michael Perkins

    Research output: Contribution to journalArticle

    8 Citations (Scopus)

    Abstract

    A model system was prepared to investigate the diastereoselectivity of the key C22-23 aldol coupling for the synthesis of spirangiens A & B. The lithium enolate of model ketone 3 was coupled with the differently protected aldehydes 4 (acetonide) and 5 (silyl) giving 3:1 and 3.5:1 dr, respectively, in favour of the unnatural (S) isomer in both cases. The lack of any significant effect on the aldol stereoselectivity induced by the aldehyde protecting groups contrasts with previous literature reports.

    Original languageEnglish
    Pages (from-to)387-394
    Number of pages8
    JournalTetrahedron
    Volume69
    Issue number1
    DOIs
    Publication statusPublished - 7 Jan 2013

    Keywords

    • Aldol reaction
    • Cytotoxic
    • Polyketide
    • Spirangien
    • Spiroacetal

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