Photochemical rearrangements of highly functionalized longipinene derivatives

被引：10
|
作者：
JosephNathan, P [1 ]
MelendezRodriguez, M [1 ]
CerdaGarciaRojas, CM [1 ]
Catalan, CAN [1 ]
机构：
[1] UNIV NACL TUCUMAN,FAC BIOQUIM QUIM & FARM,INST QUIM ORGAN,RA-4000 S MIGUEL TUCUMAN,TUCUMAN,ARGENTINA
来源：
TETRAHEDRON LETTERS | 1996年 / 37卷 / 45期
关键词：
D O I：
10.1016/0040-4039(96)01848-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Ultraviolet irradiation of 7 beta,9 alpha-diacetyloxylongipin-2-en-1-one (3) affords the vulgarone A derivative 5 and compound 7 which possesses a novel tricyclic sesquiterpene skeleton named pingilonane. The photorearrangements of 3 occur via [1,3] sigmatropic shifts of the C-4-C-10 or of the C-4-C-5 bond, respectively. Similarly, irradiation of 7 beta,8 alpha,9 alpha-triacetyloxylongipin-2-en-1-one (4) affords 6 and 8. Some biogenetic implications of these transformations are discussed. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码：8093 / 8096
页数：4
相关论文
共 50 条
  • [1] MOLECULAR-REARRANGEMENTS IN THE LONGIPINENE SERIES
    ROMAN, LU
    HERNANDEZ, JD
    CERDAGARCIAROJAS, CM
    DOMINGUEZLOPEZ, RM
    JOSEPHNATHAN, P
    JOURNAL OF NATURAL PRODUCTS, 1992, 55 (05): : 577 - 588
  • [2] Quirogane, prenopsane, and patzcuarane skeletons obtained by photochemically induced molecular rearrangements of longipinene derivatives
    Meléndez-Rodríguez, M
    Cerda-García-Rojas, CM
    Joseph-Nathan, P
    JOURNAL OF NATURAL PRODUCTS, 2002, 65 (10): : 1398 - 1411
  • [3] PHOTOCHEMICAL REARRANGEMENTS OF 18-HYDROXYLATED LANOSTEROL DERIVATIVES
    HABERMEHL, GG
    KIRSCH, JH
    REIBSTEIN, KJ
    HETEROCYCLES, 1982, 17 : 183 - 189
  • [4] Photochemical synthesis of highly functionalized cyclopropyl ketones
    Wessig, P
    Mühling, O
    HELVETICA CHIMICA ACTA, 2003, 86 (03) : 865 - 893
  • [5] Longipinene derivatives from Stevia porphyrea
    Sánchez-Arreola, E
    Cerda-García-Rojas, CM
    Román, LU
    Hernández, JD
    Joseph-Nathan, P
    PHYTOCHEMISTRY, 1999, 52 (03) : 473 - 477
  • [6] Longipinene derivatives from Santolina viscosa
    Barrero, AF
    Herrador, MM
    Alvarez-Manzaneda, RJ
    Quirós, M
    Lara, A
    del Moral, JQ
    JOURNAL OF NATURAL PRODUCTS, 2000, 63 (05): : 587 - 591
  • [7] PHOTOCHEMICAL REARRANGEMENTS AND FRAGMENTATIONS OF BENZENE-DERIVATIVES AND ANNELATED ARENES
    KAUPP, G
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1980, 19 (04) : 243 - 275
  • [8] KINETICS OF PHOTOCHEMICAL REARRANGEMENTS AND SPECTRAL BEHAVIOR OF PYRAZOLONE DERIVATIVES IN SOLUTION
    KOVALENKO, NP
    ERSHOV, YA
    ORLOVA, SF
    JOURNAL OF PHOTOCHEMISTRY, 1985, 31 (2-3): : 289 - 296
  • [9] LONGIPINENE DERIVATIVES FROM STEVIA-SERRATA
    SANCHEZARREOLA, E
    CERDAGARCIAROJAS, CM
    JOSEPHNATHAN, P
    ROMAN, LU
    HERNANDEZ, JD
    PHYTOCHEMISTRY, 1995, 39 (04) : 853 - 857
  • [10] Photochemical preparation of highly functionalized 1-indanones
    Wessig, P
    Glombitza, C
    Müller, G
    Teubner, J
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (22): : 7582 - 7591
12345