NEW SYNTHESES OF (+/-)-AMBROX, (+/-)-AMBRA OXIDE AND THEIR STEREOISOMERS

被引：24

作者：

KAWANOBE, T ^{[1
]}

KOGAMI, K ^{[1
]}

MATSUI, M ^{[1
]}

机构：

[1] TOKYO UNIV AGR, SETAGAYA KU, TOKYO 156, JAPAN

来源：

AGRICULTURAL AND BIOLOGICAL CHEMISTRY | 1986年 / 50卷 / 06期

关键词：

D O I：

10.1080/00021369.1986.10867582

中图分类号：

S3 [农学（农艺学）];

学科分类号：

0901 ;

摘要：

New and efficient syntheses of (.+-.)-ambrox (1a), (.+-.)-ambra oxide (2a) and their stereoisomers (1b, 2b .apprx. c), amber-like odorous compounds, are described. Starting from dihydro .beta.- and .alpha.-ionone (5, 12), these substances were obtained in only a few steps via stereoselective acid-catalyzed cyclization of monocyclodienoic acid (7a .apprx. b, 11a .apprx. b, 15a).

引用

页码：1475 / 1480

页数：6

共 8 条

[1] STEREOCHEMISTRY-ODOR RELATIONSHIPS IN ENANTIOMERIC AMBERGRIS FRAGRANCES
OHLOFF, G
VIAL, C
WOLF, HR
JOB, K
JEGOU, E
POLONSKY, J
LEDERER, E
[J]. HELVETICA CHIMICA ACTA, 1980, 63 (07) : 1932 - 1946
[2] Ohloff G, 1982, FRAGRANCE CHEM, P535, DOI DOI 10.1016/B978-0-12-685850-1.50020-6
[3] Information in diterpene (53 Announcement) Oxidation of sclareol with potassium permanganate
Ruzicka, L
Seidel, CF
Engel, LL
[J]. HELVETICA CHIMICA ACTA, 1942, 25 : 621 - 630
[4] SYNTHESIS OF (+/-)-NORAMBREINOLIDE BY CYCLIZATION OF TRANS-BETA-MONOCYCLOHOMOFARNESIC ACID
SAITO, A
MATSUSHITA, H
TSUJINO, Y
KANEKO, H
[J]. CHEMISTRY LETTERS, 1981, (06) : 757 - 760
[5] CYCLIZATION MECHANISM OF TRANS-BETA-MONOCYCLOHOMOFARNESIC ACID AND RELATED-COMPOUNDS
SAITO, A
MATSUSHITA, H
KANEKO, H
[J]. CHEMISTRY LETTERS, 1983, (05) : 729 - 732
[6] *ZUR KENNTNIS DER DITERPENE .62. UBER EINE NEUE, ERGIEBIGE PARTIALSYNTHESE DES AMBREINOLIDS
SCHENK, HR
GUTMANN, H
JEGER, O
RUZICKA, L
[J]. HELVETICA CHIMICA ACTA, 1952, 35 (03) : 817 - 824
[7] THE STEREOCHEMISTRY OF POLYENE CYCLIZATION
STORK, G
BURGSTAHLER, AW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (19) : 5068 - 5077
[8] VLAD PF, 1978, KHIM PRIRODNYK SOEDI, P449

← 1 →