Total Synthesis of Sphingofungin F by Orthoamide-Type Overman Rearrangement of an Unsaturated Ester

被引：33

作者：

Tsuzaki, Shun ^{[1
]}

Usui, Shunme ^{[1
]}

Oishi, Hiroki ^{[1
]}

Yasushima, Daichi ^{[1
]}

Fukuyasu, Takahiro ^{[1
]}

Oishi, Takeshi ^{[2
]}

Sato, Takaaki ^{[1
]}

Chida, Noritaka ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

[2] Keio Univ, Sch Med, Kohoku Ku, Yokohama, Kanagawa 2238521, Japan

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 07期

关键词：

ALPHA-AMINO-ACID; ASYMMETRIC-SYNTHESIS; SPHINGOSINE; INHIBITORS; CASCADE; (-)-MORPHINE; LIGANDS; ECONOMY; POTENT;

D O I：

10.1021/acs.orglett.5b00475

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of sphingofungin F through the Overman rearrangement of an unsaturated ester, which is known to be an unsuitable substrate under standard conditions due to the competitive aza-Michael reaction, is described. The developed conditions enabled the ester to be compatible with the original Overman rearrangement, providing quick access to α,α-disubstituted amino acids by minimizing extra protecting group manipulations and redox reactions. © 2015 American Chemical Society.

引用

页码：1704 / 1707

页数：4

共 50 条

[31] Second-Generation Total Synthesis of Spirastrellolide F Methyl Ester: The Alkyne Route
Benson, Stefan
Collin, Marie-Pierre
Arlt, Alexander
Gabor, Barbara
Goddard, Richard
Fuerstner, Alois
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) : 8739 - 8744
[32] TOTAL SYNTHESIS OF 19(RS)-F-LTA(4) METHYL-ESTER
GARCIA, M
DURAND, T
GIRARD, JP
ROSSI, JC
SERKOV, I
KUKLEV, D
BEZUGLOV, V
TETRAHEDRON LETTERS, 1995, 36 (36) : 6437 - 6438
[33] Synthesis of a Quaternary N,N′-Aminal-Containing A-E Ring System of Palauamine via an Enamide-Type Overman Rearrangement Reaction
Imaoka, Takuya
Iwata, Makoto
Nagasawa, Kazuo
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (20-21) : 2572 - 2578
[34] PROSTAGLANDINS .4. SYNTHESIS OF F-TYPE PROSTAGLANDINS - TOTAL SYNTHESIS OF PROSTAGLANDIN F ALPHA
MIYANO, M
MUELLER, RA
DORN, CR
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (11): : 1810 - &
[35] SYNTHESIS OF UNSATURATED AMINO-ACIDS BY [3,3]-SIGMATROPIC REARRANGEMENT OF CHELATE-BRIDGED GLYCINE ESTER ENOLATES
KAZMAIER, U
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (09): : 998 - 999
[36] Total synthesis of lycorine-type alkaloids by cyclopropyl ring-opening rearrangement
Liu, Dandan
Ai, Long
Li, Fan
Zhao, Annan
Chen, Jingbo
Zhang, Hongbin
Liu, Jianping
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (20) : 3191 - 3200
[37] TOTAL SYNTHESIS OF 12-HYDROXYMETHYLPROSTAGLANDIN F-2ALPHA METHYL-ESTER
GRIECO, PA
WANG, CLJ
OKUNIEWICZ, FJ
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (22) : 939 - 940
[38] FLUOROPROSTAGLANDINS - TOTAL SYNTHESIS OF "(+)-13-FLUOROPROSTAGLANDIN-F2-ALPHA METHYL-ESTER
GRIECO, PA
TAKIGAWA, T
VEDANANDA, TR
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (17): : 3111 - 3115
[39] The Total Synthesis of (-)-7-Deoxyloganin via N-Heterocyclic Carbene Catalyzed Rearrangement of α,β-Unsaturated Enol Esters
Candish, Lisa
Lupton, David W.
ORGANIC LETTERS, 2010, 12 (21) : 4836 - 4839
[40] BICYCLIC ENAMINES .1. REARRANGEMENT OF A QUATERNARY QUINUCLIDINE-3-CARBOXYLIC ACID ESTER AND TOTAL SYNTHESIS OF GENTIANADINE
DOLBY, J
DAHLBOM, R
HASSELGR.KH
NILSSON, JLG
ACTA CHEMICA SCANDINAVICA, 1971, 25 (02): : 735 - &

← 1 2 3 4 5 →