Organic letters

Asymmetric Synthesis of (−)-Aurantioclavine via Palladium-Catalyzed Intramolecular Allylic Amination

S Suetsugu, H Nishiguchi, C Tsukano…

Index: Suetsugu, Satoshi; Nishiguchi, Hiromi; Tsukano, Chihiro; Takemoto, Yoshiji Organic Letters, 2014 , vol. 16, # 3 p. 996 - 999

Full Text: HTML

Citation Number: 15

Abstract

The total synthesis of (−)-aurantioclavine (1) was accomplished based on an intramolecular asymmetric amination of allyl carbonate 3 containing ap-tosylamide group. The reaction using tris (dibenzylideneacetone) dipalladium (0), t Bu-phosphinooxazoline, and Bu4NCl in CH2Cl2 gave azepane 2 in 77% yield with 95% enantiomeric excess. The obtained azepane 2 was also converted to a substructure of communesin F.

Related Articles:

Pd-catalyzed enantioselective aerobic oxidation of secondary alcohols: applications to the total synthesis of alkaloids

[Krishnan, Shyam; Bagdanoff, Jeffrey T.; Ebner, David C.; Ramtohul, Yeeman K.; Tambar, Uttam K.; Stoltz, Brian M. Journal of the American Chemical Society, 2008 , vol. 130, # 41 p. 13745 - 13754]

Confirmation of the absolute configuration of (−)-aurantioclavine

[Behenna, Douglas C.; Krishnan, Shyam; Stoltz, Brian M. Tetrahedron Letters, 2011 , vol. 52, # 17 p. 2152 - 2154]

Confirmation of the absolute configuration of (−)-aurantioclavine

[Behenna, Douglas C.; Krishnan, Shyam; Stoltz, Brian M. Tetrahedron Letters, 2011 , vol. 52, # 17 p. 2152 - 2154]

Confirmation of the absolute configuration of (−)-aurantioclavine

[Behenna, Douglas C.; Krishnan, Shyam; Stoltz, Brian M. Tetrahedron Letters, 2011 , vol. 52, # 17 p. 2152 - 2154]

Confirmation of the absolute configuration of (−)-aurantioclavine

[Behenna, Douglas C.; Krishnan, Shyam; Stoltz, Brian M. Tetrahedron Letters, 2011 , vol. 52, # 17 p. 2152 - 2154]

More Articles...