Development of a Strategy for the Asymmetric Synthesis of Polycyclic Polyprenylated Acylphloroglucinols via N-Amino Cyclic Carbamate Hydrazones: Application to the Total Synthesis of (+)-Clusianone

被引：53

作者：

Garnsey, Michelle R. ^{[1
]}

Lim, Daniel ^{[1
]}

Yost, Julianne M. ^{[1
]}

Coltart, Don M. ^{[1
]}

机构：

[1] Duke Univ, Dept Chem, Durham, NC 27708 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 22期

基金：

美国国家科学基金会;

关键词：

GARSUBELLIN-A; BRIDGEHEAD LITHIATION; CLUSIANONE; (+/-)-CLUSIANONE; KETONES; BENZOPHENONES; DERIVATIVES; NEMOROSONE;

D O I：

10.1021/ol1022728

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A broadly applicable asymmetric synthetic strategy utilizing N-amino cyclic carbamate alkylation that provides access to the various stereochemical permutations of a common structural motif found in many polycyclic polyprenylated acylphloroglucinols is described. The utility of this methodology is demonstrated through the first asymmetric total synthesis of the antiviral agent (+)-clusianone.

引用

页码：5234 / 5237

页数：4

共 22 条

[1] Synthesis of polyprenylated acylphloroglucinols using bridgehead lithiation: The total synthesis of racemic clusianone and a formal synthesis of racemic garsubellin A
Ahmad, Nadia M.
Rodeschini, Vincent
Simpkins, Nigel S.
Ward, Simon E.
Blake, Alexander J.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (13) : 4803 - 4815
[2] FACILE METHOD FOR BIS-HOMOLOGATION OF KETONES TO ALPHA,BETA-UNSATURATED ALDEHYDES - APPLICATION TO SYNTHESIS OF CYCLOHEXANOID COMPONENTS OF BOLL-WEEVIL SEX ATTRACTANT
BABLER, JH
COGHLAN, MJ
[J]. SYNTHETIC COMMUNICATIONS, 1976, 6 (07) : 469 - 474
[3] Breit B, 2002, MODERN ORGANOCOPPER CHEMISTRY, P188, DOI 10.1002/3527600086.ch6
[4] Polycyclic polyprenylated acylphloroglucinols
Ciochina, Roxana
Grossman, Robert B.
[J]. CHEMICAL REVIEWS, 2006, 106 (09) : 3963 - 3986
[5] PREPARATION AND REACTIONS OF BETA-CHLORO-ALPHA,BETA-UNSATURATED KETONES
CLARK, RD
HEATHCOCK, CH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (04) : 636 - 643
[6] Nemorosone, the major constituent of floral resins of Clusia rosea
Cuesta-Rubio, O
Velez-Castro, H
Frontana-Uribe, BA
Cárdenas, J
[J]. PHYTOCHEMISTRY, 2001, 57 (02) : 279 - 283
[7] DIRECT OXIDATION OF TERTIARY ALLYLIC ALCOHOLS - SIMPLE AND EFFECTIVE METHOD FOR ALKYLATIVE CARBONYL TRANSPOSITION
DAUBEN, WG
MICHNO, DM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (04) : 682 - 685
[8] Polyprenylated benzophenones from Garcinia assigu and their potential cancer chemopreventive activities
Ito, C
Itoigawa, M
Miyamoto, Y
Onoda, S
Rao, KS
Mukainaka, T
Tokuda, H
Nishino, H
Furukawa, H
[J]. JOURNAL OF NATURAL PRODUCTS, 2003, 66 (02): : 206 - 209
[9] Total synthesis of (±)-garsubellin A
Kuramochi, A
Usuda, H
Yamatsugu, K
Kanai, M
Shibasaki, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (41) : 14200 - 14201
[10] Simple and efficient asymmetric α-alkylation and α,α-bisalkylation of acyclic ketones by using chiral N-amino cyclic carbamate hydrazones
Lim, Daniel
Coltart, Don M.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (28) : 5207 - 5210

← 1 2 3 →