Literature DB >> 21491897

Asymmetric synthesis of (+)-geranyllinaloisocyanide: assignment of absolute stereochemistry.

Yoshiyasu Ichikawa1, Yasunori Matsuda, Ken Okumura, Mitsuhiro Nakamura, Toshiya Masuda, Hiyoshizo Kotsuki, Keiji Nakano.   

Abstract

The first nonracemic synthesis of (+)-geranyllinaloisocyanide, starting with (-)-lactic acid methyl ester, has been accomplished by exploiting a [3.3] sigmatropic rearrangement of allyl cyanate. The synthesis enables assignment of the S configuration of the C(3) isocyano substituted, quaternary stereogenic center in natural geranyllinaloisocyanide.

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Year:  2011        PMID: 21491897     DOI: 10.1021/ol200308m

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  1 in total

Review 1.  Syntheses and biological studies of marine terpenoids derived from inorganic cyanide.

Authors:  Martin J Schnermann; Ryan A Shenvi
Journal:  Nat Prod Rep       Date:  2015-04       Impact factor: 13.423

  1 in total

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