Total synthesis of (+/-)-tazettine

被引：79

作者：

Rigby, JH ^{[1
]}

Cavezza, A ^{[1
]}

Heeg, MJ ^{[1
]}

机构：

[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1998年 / 120卷 / 15期

关键词：

D O I：

10.1021/ja974317j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total synthesis of (+/-)-tazettine (1) has been achieved in 16 steps from commercially available piperonyl alcohol in 11% overall yield. The crucial quaternary center was assembled by a novel [4+1] cycloaddition between dimethoxycarbene and beta-aryl vinyl isocyanate (4). Samarium diiodide conditions were employed to reduce the enamide unsaturation in the [2]benzopyrano[3,4-c]hydroindole intermediate 19 to compound 20 exhibiting a cis-AB ring fusion.

引用

页码：3664 / 3670

页数：7

共 66 条

[1] ABELMAN MM, 1990, J AM CHEM SOC, V112, P5959
[2] NEW ORGANIC COMPOUNDS FOR USE IN INSECT CONTROL
ALEXANDER, BH
GERTLER, SI
ODA, TA
BROWN, RT
IHNDRIS, RW
BEROZA, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (04) : 626 - 632
[3] [Anonymous], ALKALOIDS
[4] CYTOTOXICITY OF HYMENOCALLIS-EXPANSA ALKALOIDS
ANTOUN, MD
MENDOZA, NT
RIOS, YR
PROCTOR, GR
WICKRAMARATNE, DBM
PEZZUTO, JM
KINGHORN, AD
[J]. JOURNAL OF NATURAL PRODUCTS, 1993, 56 (08): : 1423 - 1425
[5] ELECTRON-DISTRIBUTION IN A STABLE CARBENE
ARDUENGO, AJ
DIAS, HVR
DIXON, DA
HARLOW, RL
KLOOSTER, WT
KOETZLE, TF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) : 6812 - 6822
[6] 4,7-BETA-DIMETHYL-4-AZACHOLESTAN-3-ONE (MK-386) AND RELATED 4-AZASTEROIDS AS SELECTIVE INHIBITORS OF HUMAN TYPE-1 5-ALPHA-REDUCTASE
BAKSHI, RK
PATEL, GF
RASMUSSON, GH
BAGINSKY, WF
CIMIS, G
ELLSWORTH, K
CHANG, B
BULL, H
TOLMAN, RL
HARRIS, GS
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (23) : 3871 - 3874
[7] STUDIES DIRECTED AT THE SYNTHESIS OF OPTICALLY-ACTIVE PRETAZETTINE VIA INTRAMOLECULAR NITRONE ALKENE CYCLOADDITION REACTIONS
BALDWIN, SW
AUBE, J
MCPHAIL, AT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) : 6546 - 6550
[8] TOTAL SYNTHESIS OF (+/-)-STEMODIN AND (+/-)-STEMODINONE
COREY, EJ
TIUS, MA
DAS, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (25) : 7612 - 7613
[9] 2-Alkoxy-2-amino-Delta(3)-1,3,4-oxadiazolines as novel sources of alkoxyaminocarbenes
Couture, P
Terlouw, JK
Warkentin, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (17) : 4214 - 4215
[10] TOTAL SYNTHESIS OF DL-TAZETTINE AND 6A-EPIPRETAZETTINE - A FORMAL SYNTHESIS OF DL-PRETAZETTINE - SOME OBSERVATIONS ON THE RELATIONSHIP OF 6A-EPIPRETAZETTINE AND TAZETTINE
DANISHEFSKY, S
MORRIS, J
MULLEN, G
GAMMILL, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (26) : 7591 - 7599

← 1 2 3 4 5 6 7 →