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Access to functionalized steroid side chains via modified Julia olefination.

ABSTRACT: Various functionalized steroidal side chains were conveniently accessed by a modified Julia olefination strategy using a common sulfone donor and an appropriate ?-branched aldehyde acceptor. For the coupling of these hindered classes of reaction partners (and in contrast to typically observed trends), the benzothiazolyl(BT)-sulfone anion gave superior outcomes compared to the phenyltetrazolyl(PT)-sulfone anion.

SUBMITTER: Izgu EC

PROVIDER: S-EPMC3045753 | biostudies-literature | 2011 Feb

REPOSITORIES: biostudies-literature

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Access to functionalized steroid side chains via modified Julia olefination.

Izgu Enver Cagri EC Burns Aaron C AC Hoye Thomas R TR

Organic letters 20110118 4

Various functionalized steroidal side chains were conveniently accessed by a modified Julia olefination strategy using a common sulfone donor and an appropriate α-branched aldehyde acceptor. For the coupling of these hindered classes of reaction partners (and in contrast to typically observed trends), the benzothiazolyl(BT)-sulfone anion gave superior outcomes compared to the phenyltetrazolyl(PT)-sulfone anion. ...[more]

PMID: 21244047

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