SYNTHESIS AND ABSOLUTE-CONFIGURATION OF (-)-ROTHROCKENE, A NON-HEAD-TO-TAIL MONOTERPENE

被引：22

作者：

BARBACHYN, MR ^{[1
]}

JOHNSON, CR ^{[1
]}

GLICK, MD ^{[1
]}

机构：

[1] WAYNE STATE UNIV, DEPT CHEM, DETROIT, MI 48202 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1984年 / 49卷 / 15期

关键词：

D O I：

10.1021/jo00189a020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of (-)-rothrockene, trans-1-(1-methylethenyl)-2-(2-methyl-1-propenyl)cyclopropane, and its enantiomer is described. Utilization of (-)-(R)-N,S-dimethyl-S-phenylsulfoximine in the synthesis allowed for resolution of a precursor, regio- and diastereoface selectivity in a Simmons-Smith cyclopropanation, determination of absolute configurations based on X-ray crystallography, and introduction of a side-chain double bond. The absolute configuration of the natural substance [from Artemisia tridentata rothrockii] is 1R,2S.

引用

页码：2746 / 2748

页数：3

共 10 条

[1] NEW STEREOSPECIFIC SYNTHETIC ROUTES TO TRISUBSTITUTED OLEFINS
COREY, EJ
YAMAMOTO, H
HERRON, DK
ACHIWA, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (22) : 6635 - &
[2] COREY ER, 1977, J ORGANOMET CHEM, V129, P17
[3] EPSTEIN WL, 1972, PHYTOCHEMISTRY, V12, P737
[4] TRANS-2-(2-PROPENYL)-1-(2-METHYL-1-PROPENYL)CYCLOPROPANE (ROTHROCKENE) - A NON HEAD TO TAIL MONOTERPENOID WITH A NEW SKELETAL SYSTEM FROM ARTEMISIA-TRIDENTATA ROTHROCKII
EPSTEIN, WW
GAUDIOSO, LA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (01) : 175 - 176
[5] EPSTEIN WW, COMMUNICATION
[6] SYNTHESIS OF ALKENES BY REDUCTIVE ELIMINATION OF BETA-HYDROXYSULFOXIMINES
JOHNSON, CR
KIRCHHOFF, RA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (13) : 3602 - 3607
[7] BETA-HYDROXYSULFOXIMINE-DIRECTED SIMMONS-SMITH CYCLOPROPANATIONS - SYNTHESIS OF (-)-THUJOPSENE AND (+)-THUJOPSENE
JOHNSON, CR
BARBACHYN, MR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (15) : 4290 - 4291
[8] NUCLEOPHILIC-SUBSTITUTION AT SULFUR IN SULFONIMIDOYL COMPOUNDS - SYNTHESIS OF SULFOXIMINES
JOHNSON, CR
JONSSON, EU
WAMBSGANS, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (13) : 2061 - 2065
[9] RATIER M, 1978, J CHEM RES-S, P179
[10] Simmons H.E., 1972, ORG REACT, V20, P1

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