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Synthesis of cis ‐Enediynes from 1,5‐Diynes by Rearrangement of an Allylic Double Bond
Author(s) -
Dai WeiMin,
Fong Kin Chiu,
Danjo Hiroshi,
Nishimoto Seiichi
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199607791
Subject(s) - enediyne , allylic rearrangement , chemistry , double bond , nucleophile , stereochemistry , catalysis , organic chemistry
Simple rearrangement yields enediynes selectively! Rearrangement of the allylic double bond in compounds of type 1 yields the cis ‐enediynes 2 selectively. Cycloaromatization of 2 (R 1 = CH 2 SO 2 Ph) affords reactive diradicals analogous to those formed from the natural enediyne antitumor antibiotics. Nu = nucleophile.