The enantiomeric 2-azapinanes, aza analogues of the pinyl carbocation intermediates in pinene biosynthesis, were synthesized from (-)- and (+)-cis-pinonic acids. The individual reactions in the 5-step sequence were Beckmann rearrangement of the pinonic acid oximes, cyclization to the N-acetyl lactams, hydrolysis to the NH-lactams, N-methylations, and LiAlH(4) reductions. The anti stereochemistry of the N-methyl groups in the salts with respect to the gem-dimethyl bridge was established by NOE measurements and by X-ray diffraction analysis.
The enantiomeric 2-azapinanes, n class="Chemical">aza analogues of the pinyl carbocation intermediates in pinene biosynthesis, were synthesized from (-)- and(+)-cis-pinonic acids. The individual reactions in the 5-step sequence were Beckmann rearrangement of the pinonic acid oximes, cyclization to the N-acetyl lactams, hydrolysis to the NH-lactams, N-methylations, and LiAlH(4) reductions. The anti stereochemistry of the N-methyl groups in the salts with respect to the gem-dimethyl bridge was established by NOE measurements and by X-ray diffraction analysis.
Authors: Douglas A Whittington; Mitchell L Wise; Marek Urbansky; Robert M Coates; Rodney B Croteau; David W Christianson Journal: Proc Natl Acad Sci U S A Date: 2002-11-13 Impact factor: 11.205
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Authors: Christoph Gaul; Jón T Njardarson; Dandan Shan; David C Dorn; Kai-Da Wu; William P Tong; Xin-Yun Huang; Malcolm A S Moore; Samuel J Danishefsky Journal: J Am Chem Soc Date: 2004-09-15 Impact factor: 15.419