Asymmetric Total Synthesis of Caribenol A via an Intramolecular Diels-Alder Reaction

被引：22

作者：

Han, Jing-Chun ^{[1
]}

Liu, Lian-Zhu ^{[1
]}

Chang, Yuan-Yuan ^{[1
]}

Yue, Guo-Zong ^{[1
]}

Guo, Jie ^{[1
]}

Zhou, Li-Yan ^{[1
]}

Li, Chuang-Chuang ^{[1
]}

Yang, Zhen ^{[1
,2
,3
]}

机构：

[1] Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China

[2] Peking Univ, Coll Chem, Peking Tsinghua Ctr Life Sci, Minist Educ,Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China

[3] Peking Univ, Coll Chem, Peking Tsinghua Ctr Life Sci, BNLMS, Beijing 100871, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 11期

基金：

美国国家科学基金会;

关键词：

5-7-6 TRICYCLIC CORE; STEREOSELECTIVE-SYNTHESIS; DITERPENE; GUANACASTEPENE; CONSTRUCTION; HYDROXYLATION; DIMERIZATION; OXIDATION; ALKALOIDS; PROGRESS;

D O I：

10.1021/jo4006156

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of the caribenol A (1), a novel natural product with an intriguing tetracyclic framework, has been achieved. The synthesis features an intramolecular Diels-Alder (IMDA) reaction for the facile construction of the tricyclic [5-7-6] skeleton of caribenol A (1) and a biomimetic oxidation reaction for the formation of the 2-hydroxyfuran-2(5H)-one motif of caribenol A (1) as key steps. This synthetic approach also reveals that the sp(2) carbon at C(2) in substrate 8 is a critical factor for the formation of the tricyclic [5-7-6] skeleton in 7.

引用

页码：5492 / 5504

页数：13

共 50 条

[21] Synthesis of the tricyclic core of vinigrol via an intramolecular Diels-Alder reaction
Grise, Christiane M.
Tessier, Guillaume
Barriault, Louis
ORGANIC LETTERS, 2007, 9 (08) : 1545 - 1548
[22] THE INTRAMOLECULAR DIELS-ALDER REACTION
BRIEGER, G
BENNETT, JN
CHEMICAL REVIEWS, 1980, 80 (01) : 63 - 97
[23] DIELS-ALDER REACTION IN PARTIAL ASYMMETRIC SYNTHESIS
KOROLEV, AI
MUR, VI
AVAKYAN, VG
JOURNAL OF GENERAL CHEMISTRY USSR, 1964, 34 (02): : 713 - &
[24] Intramolecular Diels-Alder reaction, part 4 -: Formal total synthesis of (+)-dihydromevinolin via a chelate-controlled intramoleenlar Diels-Alder reaction as the key step
Schnaubelt, J
Frey, B
Reissig, HU
HELVETICA CHIMICA ACTA, 1999, 82 (05) : 666 - 676
[25] PARTIAL ASYMMETRIC SYNTHESIS IN DIELS-ALDER REACTION
WALBORSKY, HM
DAVIS, TC
BARASH, L
TETRAHEDRON, 1963, 19 (12) : 2333 - &
[26] TOTAL SYNTHESIS OF (-)-NUPHARAMINE AND (+)-3-EPINUPHARAMINE VIA ASYMMETRIC NITROSO DIELS-ALDER REACTION
AOYAGI, S
SHISHIDO, Y
KIBAYASHI, C
TETRAHEDRON LETTERS, 1991, 32 (34) : 4325 - 4328
[27] Isoindolone Formation via Intramolecular Diels-Alder Reaction
Ball, Matthew
Boyd, Alistair
Churchill, Gwydion
Cuthbert, Murray
Drew, Mark
Fielding, Mark
Ford, Gair
Frodsham, Lianne
Golden, Michael
Leslie, Kevin
Lyons, Sarah
McKeever-Abbas, Ben
Stark, Andrew
Tomlin, Paula
Gottschling, Stephen
Hajar, Abraham
Jiang, Ji-long
Lo, Josephine
Suchozak, Bob
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (05) : 741 - 747
[28] Total synthesis of elisabethin A: Intramolecular Diels-Alder reaction under biomimetic conditions
Heckrodt, TJ
Mulzer, J
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (16) : 4680 - 4681
[29] Recent applications of intramolecular Diels-Alder reaction in total synthesis of natural products
Heravi, Majid M.
Vavsari, Vaezeh Fathi
RSC ADVANCES, 2015, 5 (63) : 50890 - 50912
[30] PRACTICAL TOTAL SYNTHESIS OF LUOTONIN A BY INTRAMOLECULAR DOUBLE HETERO DIELS-ALDER REACTION
Natsuki, Ken
Shindo, Tadamichi
Toyota, Masahiro
HETEROCYCLES, 2012, 84 (02) : 1301 - 1304

← 1 2 3 4 5 →