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Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane.

ABSTRACT: [reaction: see text] A total synthesis of (+)-bullatacin has been accomplished via a diastereoselective [3+2] annulation reaction of the highly enantiomerically enriched allylsilane 3 and racemic aldehyde 4, which provides the key bis-tetrahydrofuran fragment 15 with > or = 20:1 ds.

SUBMITTER: Tinsley JM

PROVIDER: S-EPMC2507730 | biostudies-literature | 2005 Sep

REPOSITORIES: biostudies-literature

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Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane.

Tinsley Jennifer M JM Mertz Eric E Chong Pek Y PY Rarig Robert-André F RA Roush William R WR

Organic letters 20050901 19

[reaction: see text] A total synthesis of (+)-bullatacin has been accomplished via a diastereoselective [3+2] annulation reaction of the highly enantiomerically enriched allylsilane 3 and racemic aldehyde 4, which provides the key bis-tetrahydrofuran fragment 15 with > or = 20:1 ds. ...[more]

PMID: 16146398

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