A Successful Route to Strychnine

The conjugate addition substrate that we were considering bore an obvious resemblance to Stork s however, it would incorporate a free NH and OH, as well as a more sensitive aldehyde. In this light, an approach involving reactive organolithium species seemed unlikely to be successful, and a few experiments quickly validated this surmise. We therefore sought a precursor that could 

As a result of the excellent precedent from the Takeda and Smith groups, we targeted vinylsilane 136 as a key intermediate in a Brook rearrangement/conjugate 

4 (a) For a relevant discussion of the difficulty of C15-C20 bond construction, see [lOi] and [65a]. (b) For a discussion of D-ring formation in related pyrroloindoline natural products, see [20d], 

Acknowledgment We dedicate this account to the memory of David Gin, a wonderful person and truly inspiring scientist. We thank the NSF (CAREER Award CHE-0847061) for support of our work. This project also benefited from support through graduate fellowships to D.B.C.M. from Eli Lilly, the NSERC of Canada, and Bristol-Myers Squibb, as well as an Amgen Young Investigator 

an AstraZeneca Award for Excellence in Chemistry, and an Eli Lilly Grantee Award to C. D.V. D.B.C.M is a recipient of a Roche Excellence in Chemistry Award, and C.D.V. is a fellow of the A.P. Sloan Foundation and is a University of California, Irvine Chancellor s Faculty Fellow. 

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