ARENAROL AND ARENARONE - SESQUITERPENOIDS WITH REARRANGED DRIMANE SKELETONS FROM THE MARINE SPONGE DYSIDEA-ARENARIA

被引：79
作者：
SCHMITZ, FJ
LAKSHMI, V
POWELL, DR
VANDERHELM, D
机构：
[1] Department of Chemistry, University of Oklahoma, Norman, Oklahoma
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1984年 / 49卷 / 02期
关键词：
D O I：
10.1021/jo00176a005
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two new sesquiterpenoids, arenarol (3a) and arenarone (4), having identical rearranged drimane skeletons bearing hydroquinol and hydroquinone moieties, respectively, are reported from the Pacific sponge Dysidea arenaria. The structure of arenarol was determined by X-ray analysis of its diacetate which crystallizes in the space group P212121 with unit-cell dimensions (138 K) a = 9.964 (5), b = 6.81 (2), and c = 33.33 (5) Å. The crystal structure was determined from 2268 data. The final R value is 0.065. Arenarol was chemically correlated with arenarone by silver oxide oxidation. Detailed 400-MHz 1H NMR analysis of arenarol assisted by 2-D (/-resolved and 2-D homocorrelation spectroscopy is tabulated. © 1984, American Chemical Society. All rights reserved.
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页码：241 / 244
页数：4
相关论文
共 18 条
[1]   CORRELATION OF PROTON CHEMICAL-SHIFTS BY TWO-DIMENSIONAL FOURIER-TRANSFORM NMR [J].
BAX, A ;
FREEMAN, R ;
MORRIS, G .
JOURNAL OF MAGNETIC RESONANCE, 1981, 42 (01) :164-168
[2]  
BAX A, 1982, 2 DIMENSIONAL NUCLEA
[3]   X-RAY SCATTERING FACTORS COMPUTED FROM NUMERICAL HARTREE-FOCK WAVE FUNCTIONS [J].
CROMER, DT ;
MANN, JB .
ACTA CRYSTALLOGRAPHICA SECTION A-CRYSTAL PHYSICS DIFFRACTION THEORETICAL AND GENERAL CRYSTALLOGRAPHY, 1968, A 24 :321-&
[4]  
deRosa S., 1976, J CHEM SOC P1, P1408
[5]  
DHALL L, 1980, J AM CHEM SOC, V102, P5703
[6]  
FAULKNER DJ, COMMUNICATION
[7]   ZONAROL AND ISOZONAROL, FUNGITOXIC HYDROQUINONES FROM BROWN SEAWEED DICTYOPTERIS-ZONARIOIDES [J].
FENICAL, W ;
SIMS, JJ ;
SQUATRITO, D ;
WING, RM ;
RADLICK, P .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (13) :2383-2386
[8]   CHROMAZONAROL AND ISOCHROMAZONAROL, NEW CHROMANOLS FROM BROWN SEAWEED DICTYOPTERIS-UNDULATA(ZONARIOIDES) [J].
FENICAL, W ;
MCCONNELL, O .
EXPERIENTIA, 1975, 31 (09) :1004-1005
[9]  
GUERAN RI, 1972, CANCER CHERMOTHER RE, V3, P1
[10]  
HIGA T, 1981, MARINE NATURAL PRODU, V4, pCH3
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