83650-13-9Relevant academic research and scientific papers
11-Step Total Synthesis of (-)-Maoecrystal v
Cernijenko, Artiom,Risgaard, Rune,Baran, Phil S.
supporting information, p. 9425 - 9428 (2016/08/11)
An expedient, practical, and enantioselective route to the highly congested ent-kaurane diterpene maoecrystal V is presented. This route, which has been several years in the making, is loosely modeled after a key pinacol shift in the proposed biosynthesis. Only 11 steps, many of which are strategic in that they build key skeletal bonds and incorporate critical functionalities, are required to access (-)-maoecrystal V. Several unique and unexpected maneuvers are featured in this potentially scalable pathway. Reevaluation of the biological activity calls into question the initial exuberance surrounding this natural product.
Organozinc reagents in synthesis: The facile generation of 2-(trialkylsilyl)prop-2-enylzinc from 2-bromo-1-trimethylsilylprop-2-ene
Eshelby, James J.,Parsons, Philip J.,Crowley, Patrick J.
, p. 191 - 199 (2007/10/03)
A range of electrophiles react with 2-(trimethylsilyl)prop-2-enylzinc chloride, which is prepared by sequentially treating 2-bromo-1-trimethylsilylprop-2-ene with ButLi and then zinc chloride. The addition of transition metal catalysts can alter the reactivity of the organometallic compound from prop-2-enylation to prop-1-en-2-ylation.
