Total synthesis of norzoanthamine

被引：195

作者：

Miyashita, M ^{[1
]}

Sasaki, M ^{[1
]}

Hattori, I ^{[1
]}

Sakai, M ^{[1
]}

Tanino, K ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 0600810, Japan

来源：

SCIENCE | 2004年 / 305卷 / 5683期

关键词：

D O I：

10.1126/science.1098851

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Norzoanthamine, an alkaloid isolated from Zoanthus sp., can suppress the loss of bone weight and strength in ovariectomized mice. Norzoanthamine derivatives can also strongly inhibit the growth of P-388 murine leukemia cell lines and human platelet aggregation. However, norzoanthamine's densely functionalized complex stereostructure and scarce availability from natural sources have proved a synthetic challenge. We report the stereoselective total synthesis of norzoanthamine in 41 steps, with an overall yield of 3.5% ( an average of 92% yield each step).

引用

页码：495 / 499

页数：5

共 38 条

[1] TOTAL SYNTHESIS OF CRYSTALLINE (+/-)-FREDERICAMYCIN-A - USE OF RADICAL SPIROCYCLIZATION
CLIVE, DLJ
TAO, Y
KHODABOCUS, A
WU, YJ
ANGOH, AG
BENNETT, SM
BODDY, CN
BORDELEAU, L
KELLNER, D
KLEINER, G
MIDDLETON, DS
NICHOLS, CJ
RICHARDSON, SR
VERNON, PG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (25) : 11275 - 11286
[2] PROTECTING GROUP IMPROVEMENT BY ISOTOPIC-SUBSTITUTION - SYNTHESIS OF THE QUINONE SYSTEM OF FREDERICAMYCIN-A
CLIVE, DLJ
CANTIN, M
KHODABOCUS, A
KONG, XL
TAO, Y
[J]. TETRAHEDRON, 1993, 49 (36) : 7917 - 7930
[3] New alkaloids from a marine zoanthid
Daranas, AH
Fernández, JJ
Gavín, JA
Norte, M
[J]. TETRAHEDRON, 1999, 55 (17) : 5539 - 5546
[4] Epioxyzoanthamine, a new zoanthamine-type alkaloid and the unusual deuterium exchange in this series.
Daranas, AH
Fernández, JJ
Gavín, JA
Norte, M
[J]. TETRAHEDRON, 1998, 54 (27) : 7891 - 7896
[5] Fukuzawa S., 1995, HETEROCYCL COMMUN, V1, P207
[6] Stereoselective synthesis of the ABC ring system of norzoanthamine
Ghosh, S
Rivas, F
Fischer, D
González, MA
Theodorakis, EA
[J]. ORGANIC LETTERS, 2004, 6 (06) : 941 - 944
[7] Hikage N, 2000, CHEM PHARM BULL, V48, P1370
[8] Synthetic studies of zoanthamine/norzoanthamine alkaloids: Construction of the heterocyclic aminal core (CDEFG ring)
Hikage, N
Furukawa, H
Takao, K
Kobayashi, S
[J]. TETRAHEDRON LETTERS, 1998, 39 (34) : 6241 - 6244
[9] Synthetic studies of zoanthamine/norzoanthamine alkaloids: Advanced intermediate for the heterocyclic aminal core
Hikage, N
Furukawa, H
Takao, K
Kobayashi, S
[J]. TETRAHEDRON LETTERS, 1998, 39 (34) : 6237 - 6240
[10] Construction of the benzylic quaternary carbon center of zoanthenol by intramolecular Mizoroki-Heck reaction of enone
Hirai, G
Koizumi, Y
Moharram, SM
Oguri, H
Hirama, M
[J]. ORGANIC LETTERS, 2002, 4 (09) : 1627 - 1630

← 1 2 3 4 →