Alkyne of magic: An efficient synthesis of (+)-spirolaxine methyl ether (1) was accomplished by using alkynes as versatile synthetic building blocks. Highlights include two ProPhenol-catalyzed asymmetric alkynylations and a Pd-catalyzed spiroketalization (see scheme; TBS=tert-butyldiphenylsilyl). The use of alkynes alleviates the chemoselectivity issues of ketones and should be widely applicable to natural product synthesis.
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Trost et al. (2007) studied this question.
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