De novo asymmetric synthesis of anamarine and its analogues

被引：39

作者：

Gao, D ^{[1
]}

O'Doherty, GA ^{[1
]}

机构：

[1] W Virginia Univ, Dept Chem, Morgantown, WV 26506 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 24期

关键词：

D O I：

10.1021/jo051681p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective synthesis of anamarine has been achieved in 21 steps. The route relies on enantio- and regioselective Sharpless dihydroxylation of dienoate ester and zinc borohydride reduction to establish the C-8-C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route has also been used to prepare two diastereoisomers of anamarine in 14 steps.

引用

页码：9932 / 9939

页数：8

共 50 条

[21] Asymmetric synthesis of warfarin and its analogues on water
Rogozinska-Szymczak, Maria
Mlynarski, Jacek
TETRAHEDRON-ASYMMETRY, 2014, 25 (10-11) : 813 - 820
[22] THE SYNTHESIS OF (-)-ANAMARINE
VALVERDE, S
HERNANDEZ, A
HERRADON, B
RABANAL, RM
MARTINLOMAS, M
TETRAHEDRON, 1987, 43 (15) : 3499 - 3504
[23] DE NOVO ASYMMETRIC SYNTHESIS OF THE PYRANOSES: FROM MONOSACCHARIDES TO OLIGOSACCHARIDES
Aljahdali, Alhanouf Z.
Shi, Pei
Zhong, Yashan
O'Doherty, George A.
ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, VOL 69, 2013, 69 : 55 - 123
[24] Regioselective Bromination Tactics in the de Novo Synthesis of Chlorophyll b Analogues
Muthiah, Chinnasamy
Lahaye, Dorothee
Taniguchi, Masahiko
Ptaszek, Marcin
Lindsey, Jonathan S.
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (09): : 3237 - 3247
[25] De novo asymmetric synthesis of cladospolide B-D
Xing, Yalan
O'Doherty, George A.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
[26] De novo asymmetric synthesis of anthrax tetrasaccharide and related tetrasaccharide
Guo, Haibing
O'Doherty, George A.
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14): : 5211 - 5220
[27] De novo asymmetric synthesis of 8a-epi-swainsonine
Abrams, Jason N.
Babu, Ravula Satheesh
Guo, Haibing
Le, Dianna
Le, Jennifer
Osbourn, Joshua M.
O'Doherty, George A.
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (05): : 1935 - 1940
[28] De Novo Asymmetric Synthesis of Avocadyne, Avocadene, and Avocadane Stereoisomers
Cunha, Vitor L. S.
Liu, Xiaofan
Lowary, Todd L.
O'Doherty, George A.
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (23): : 15718 - 15725
[29] Stereoselective synthesis of anamarine
Díaz-Oltra, S
Murga, J
Falomir, E
Carda, M
Marco, JA
TETRAHEDRON, 2004, 60 (13) : 2979 - 2985
[30] Asymmetric De Novo Synthesis of a Cucurbitane Triterpenoid: Total Synthesis of Octanorcucurbitacin B
Bucknam, Andrea R.
Micalizio, Glenn C.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (19) : 8493 - 8497

← 1 2 3 4 5 →