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Stereochemical Control in the Conjugate Reduction and A New Method forcis-α-Methylene-γ-butyrolactone Formation

1979; Oxford University Press; Volume: 43; Issue: 10 Linguagem: Inglês

10.1080/00021369.1979.10863757

1881-1280

Minoru Isobe, Hideo Iio, Toshio Goto,

Advanced Synthetic Organic Chemistry

The mechanism of the stereospecific hydride conjugate addition of 7 concerned in the total synthesis of vernolepin (1) was confirmed from the fact that intramolecular hydride attack was only possible by coordinating with the two axial hydroxyl groups present. This confirmation led us to develop a new general method for stereospecific preparation of cis-fused α-methylene-γ-butyrolactones.