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
  • [41] STRUCTURAL AND STEREOCHEMICAL STUDIES OF NATURALLY-OCCURRING LONGIPINENE DERIVATIVES
    ROMAN, LU
    DELRIO, RE
    HERNANDEZ, JD
    CERDA, CM
    CERVANTES, D
    CASTANEDA, R
    JOSEPHNATHAN, P
    JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (21): : 3965 - 3972
  • [42] Absolute configuration of the α-methylbutyryl residue in longipinene derivatives from Stevia pilosa
    Alvarez-García, R
    Torres-Valencia, J
    Román, LU
    Hernández, JD
    Cerda-García-Rojas, CM
    Joseph-Nathan, P
    PHYTOCHEMISTRY, 2005, 66 (06) : 639 - 642
  • [43] PHOTOCHEMICAL REARRANGEMENTS OF "5,6-EPIMINO-5,6-DIHYDRO-BETA-IONONE AND DERIVATIVES
    MULLER, EP
    HELVETICA CHIMICA ACTA, 1986, 69 (03) : 692 - 697
  • [44] THERMAL AND PHOTOCHEMICAL REARRANGEMENTS OF DIVINYLCYCLOPROPANES TO CYCLOHEPTADIENES - MODEL FOR BIOSYNTHESIS OF CYCLOHEPTADIENE DERIVATIVES FOUND IN A SEAWEED (DICTYOPTERIS)
    PICKENHAGEN, W
    NAF, F
    OHLOFF, G
    MULLER, P
    PERLBERGER, JC
    HELVETICA CHIMICA ACTA, 1973, 56 (06) : 1868 - 1874
  • [45] ASYMMETRIC SYNTHESES OF HIGHLY FUNCTIONALIZED BICYCLO[2.2.2]OCTENE DERIVATIVES
    Iwatsu, Masafumi
    Urabe, Daisuke
    Inoue, Masayuki
    HETEROCYCLES, 2010, 82 (01) : 491 - 504
  • [46] HIGHLY STEREOSELECTIVE ROUTES TO FUNCTIONALIZED GEMINAL ALKYL DERIVATIVES OF CARBOHYDRATES
    FRASERREID, B
    TSANG, R
    TULSHIAN, DB
    SUN, M
    JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (18): : 3764 - 3767
  • [47] Phosphine-catalyzed synthesis of highly functionalized coumarin derivatives
    Henry, Christopher E.
    Kwon, Ohyun
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [48] A green and efficient method for the synthesis of highly functionalized selenazole derivatives
    Pourmosavi, Marziyeh
    Mosslemin, Mohammad H.
    Hassanabadi, Alireza
    INORGANIC AND NANO-METAL CHEMISTRY, 2022, 52 (05) : 706 - 710
  • [49] PHOTOCHEMICAL REARRANGEMENTS OF SUBSTITUTED THIOCHROMANONE SULFOXIDES
    STILL, IWJ
    ARORA, PC
    CHAUHAN, MS
    KWAN, MH
    THOMAS, MT
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1976, 54 (03): : 455 - 470
  • [50] PHOTOCHEMICAL REARRANGEMENTS OF SOME PHOTOCHROMIC FULGIMIDES
    HART, RJ
    HELLER, HG
    SALISBUR.K
    CHEMICAL COMMUNICATIONS, 1968, (24) : 1627 - +
12345