Synthesis of (1 alpha,7 alpha,8 beta)-(+/-)-8-methyl-2-methylenebicyclo[5.3.0]dec-5-en-8-ol. Structure revision of natural dictamnol

被引：0
|
作者：
Piet, DP [1 ]
Orru, RVA [1 ]
Jenniskens, LHD [1 ]
vandeHaar, C [1 ]
vanBeek, TA [1 ]
Franssen, MCR [1 ]
Wijnberg, JBPA [1 ]
deGroot, A [1 ]
机构：
[1] AGR UNIV WAGENINGEN, DEPT ORGAN CHEM, NL-6703 HB WAGENINGEN, NETHERLANDS
来源：
CHEMICAL & PHARMACEUTICAL BULLETIN | 1996年 / 44卷 / 07期
关键词：
Dictamnus dasycarpus; dictamnol; structure revision; pregeijerene; cyclization;
D O I：
暂无
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The total synthesis of the title compound (+/-)-1 is described, The key step in the synthesis of this cis-fused trinor-guaiane is the base-induced and -directed rearrangement of the tosylate ester 4. Because of differences in the spectral data of synthetic (+/-)-1 and natural dictamnol, a trinor-guaiane isolated from Dictamnus dasycarpus TURCZ., a revised structure for the natural product is proposed, Nuclear Overhauser effect (NOE) difference experiments and a detailed investigation of the air-induced cyclization reaction of pregeijerene, isolated from Amyris diatrypa SPRENGEL, support the structure revision of natural dictamnol.
引用
收藏
页码：1400 / 1403
页数：4
相关论文
共 50 条
12345