A Novel Three??Carbon Ring Expansion Sequence Synthesis of Exaltone® and (±)??Muscone
C Fehr
Index: Fehr, Charles Helvetica Chimica Acta, 1983 , vol. 66, # 8 p. 2512 - 2518
Full Text: HTML
Citation Number: 21
Abstract
Abstract Intramolecular Grignard-type reaction of the bromo lactones 3 and 8 affords the macrocycles 10, 11, 12 and 13, 14, 15, respectively. More efficiently, 10 and 13 are obtained by intramolecular nucleophilic attack of the carbanions derived from the sulfonyl lactones 20
Related Articles:
Olefinic cyclization promoted by beckmann rearrangement of oxime sulfonate synthesis of dl-muscone
[Sakane, Soichi; Maruoka, Keiji; Yamamoto, Hisashi Tetrahedron Letters, 1983 , vol. 24, # 9 p. 943 - 946]
A Short Synthesis of (±)??Muscone
[Rautenstrauch, Valentin; Snowden, Roger L.; Linder, Simon M. Helvetica Chimica Acta, 1990 , vol. 73, # 4 p. 896 - 901]
Free radical ring expansion and rearrangement of large carbocyclic rings
[Dowd, Paul; Choi, Soo-Chang Tetrahedron Letters, 1991 , vol. 32, # 5 p. 565 - 568]
[Tsuji, Hayato; Yamagata, Ken-Ichi; Itoh, Yoshimitsu; Endo, Kohei; Nakamura, Masaharu; Nakamura, Eiichi Angewandte Chemie - International Edition, 2007 , vol. 46, # 42 p. 8060 - 8062]
[Wender, Paul A.; Holt, Dennis A.; Sieburth, Scott M. Journal of the American Chemical Society, 1983 , vol. 105, # 10 p. 3348 - 3350]