Asymmetric Synthesis of (-)-Martinellic Acid

被引：39

作者：

Davies, Stephen G. ^{[1
]}

Fletcher, Ai M. ^{[1
]}

Lee, James A. ^{[1
]}

Lorkin, Thomas J. A. ^{[1
]}

Roberts, Paul M. ^{[1
]}

Thomson, James E. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 08期

关键词：

CYCLIZATION-ELIMINATION REACTION; FORMAL TOTAL-SYNTHESIS; PURE LITHIUM AMIDES; CONJUGATE ADDITION; MARTINELLIC ACID; RADICAL-ADDITION; TRICYCLIC CORE; NUCLEOPHILIC-SUBSTITUTION; ALKALOIDS MARTINELLINE; CYCLOADDITION APPROACH;

D O I：

10.1021/ol4007508

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A high-yielding total asymmetric synthesis of (-)-martinellic acid is reported. The conjugate addition of lithium (R)-N-allyl-N-(alpha-methyl-4-methoxybenzyl)amide to tert-butyl (E)-3[2'-(N,N-diallylamino)-5'-bromophenyl]propenoate and alkylation of the resultant beta-amino ester have been used as the key steps to install the C(9b) and C(3a) stereogenic centers, respectively, and a highly diastereoselective Wittig reaction/intramolecular Michael addition was then used to create the C(4) stereogenic center within this tricyclic molecular architecture.

引用

页码：2050 / 2053

页数：4

共 50 条

[31] Total synthesis of the alkaloids martinelline and martinellic acid via a hetero Diels-Alder multicomponent coupling reaction
Powell, DA
Batey, RA
ORGANIC LETTERS, 2002, 4 (17) : 2913 - 2916
[32] An improved synthesis of (-)-martinellic acid via radical addition - Cyclization-elimination reaction of chiral oxime ether
Miyata, O
Shirai, A
Yoshino, S
Takeda, Y
Sugiura, M
Naito, T
SYNLETT, 2006, (06) : 893 - 896
[33] Asymmetric synthesis of β-amino acid scaffolds
Bull, SD
Davies, SG
Smith, AD
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, Royal Society of Chemistry (22): : 2931 - 2938
[34] Asymmetric total synthesis of antiochic acid
Zhao, Yu-Jun
Loh, Teck-Peng
ORGANIC LETTERS, 2008, 10 (11) : 2143 - 2145
[35] Asymmetric Synthesis of Pipecolic Acid and Derivatives
Cant, Alastair A.
Sutherland, Andrew
SYNTHESIS-STUTTGART, 2012, 44 (13): : 1935 - 1950
[36] AN ASYMMETRIC-SYNTHESIS OF CROBARBATIC ACID
CHEN, MY
FANG, JM
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10): : 2937 - 2941
[37] ASYMMETRIC-SYNTHESIS OF LYCOPERDIC ACID
YOSHIFUJI, S
KANAME, M
CHEMICAL & PHARMACEUTICAL BULLETIN, 1995, 43 (10) : 1617 - 1620
[38] Asymmetric total synthesis of pinnaic acid
Xu, Shu
Arimoto, Hirokazu
Uemura, Daisuke
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (30) : 5746 - 5749
[39] Asymmetric Synthesis of Homocitric Acid Lactone
Nickerson, Leslie A.
Huynh, Valerie
Balmond, Edward I.
Cramer, Stephen P.
Shaw, Jared T.
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (22): : 11404 - 11408
[40] The asymmetric total synthesis of (+)-salvianolic acid A
Zheng, Yong
Song, Wei-Bin
Xuan, Li-Jiang
TETRAHEDRON, 2016, 72 (33) : 5047 - 5050

← 1 2 3 4 5 →