Structural and stereochemical reassessment of sclerophytin-type diterpenes

被引:20
作者
Friedrich, D [1 ]
Paquette, LA [1 ]
机构
[1] Ohio State Univ, Evans Chem Labs, Columbus, OH 43210 USA
来源
JOURNAL OF NATURAL PRODUCTS | 2002年 / 65卷 / 02期
关键词
D O I
10.1021/np0103822
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Marine invertebrates are a rich source of oxygenated diterpenoids.(1-4) Among those isolated from the soft coral Sclerophyturn capitalis are sclerophytins A and B, originally formulated by their discoverers as 1 and 2.(5) The novel structural features of these oxygen-bridged heterocycles and the significant cytotoxic properties of 1 have attracted some defining synthetic work.(6-9) In consideration of the fact that synthetic 3 and 4 both proved to differ significantly from the originally isolated marine metabolites, an extensive N'MR analysis of 2 was undertaken, the results of which identified sclerophytin B to be 6.(10) This thorough investigation also implicated sclerophytin A to be 5 since its simple acetylation leads to 6.(5,7,8).
引用
收藏
页码:126 / 130
页数:5
相关论文
共 18 条
[1]   SCLEROPHYTIN C-F - ISOLATION AND STRUCTURES OF 4 NEW DITERPENES FROM THE SOFT CORAL SCLEROPHYTUM-CAPITALIS [J].
ALAM, M ;
SHARMA, P ;
ZEKTZER, AS ;
MARTIN, GE ;
JI, XH ;
VANDERHELM, D .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (08) :1896-1900
[2]   Total asymmetric synthesis of the putative structure of the cytotoxic diterpenoid (-)-sclerophytin A and of the authentic natural sclerophytins A and B [J].
Bernardelli, P ;
Moradei, OA ;
Friedrich, D ;
Yang, J ;
Gallou, F ;
Dyck, BP ;
Doskotch, RW ;
Lange, T ;
Paquette, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :9021-9032
[3]  
Bernardelli P, 1998, HETEROCYCLES, V49, P531
[4]   THE CHEMISTRY AND CHEMICAL ECOLOGY OF OCTOCORALS (COELENTERATA, ANTHOZOA, OCTOCORALLIA) [J].
COLL, JC .
CHEMICAL REVIEWS, 1992, 92 (04) :613-631
[5]   Marine natural products [J].
Faulkner, DJ .
NATURAL PRODUCT REPORTS, 1997, 14 (03) :259-302
[6]   Revised constitution of sclerophytins A and B [J].
Friedrich, D ;
Doskotch, RW ;
Paquette, LA .
ORGANIC LETTERS, 2000, 2 (13) :1879-1882
[7]   Enantioselective syntheses of authentic sclerophytin A, sclerophytin B, and cladiell-11-ene-3,6,7-triol [J].
Gallou, F ;
MacMillan, DWC ;
Overman, LE ;
Paquette, LA ;
Pennington, LD ;
Yang, J .
ORGANIC LETTERS, 2001, 3 (01) :135-137
[8]   A general strategy for the synthesis of cladiellin diterpenes: Enantioselective total syntheses of 6-acetoxycladiell-7(16),11-dien-3-ol (deacetoxyalcyonin acetate), cladiell-11-ene-3,6,7-triol, sclerophytin A, and the initially purported structure of sclerophytin A [J].
MacMillan, DWC ;
Overman, LE ;
Pennington, LD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :9033-9044
[9]   BIOACTIVE TERPENOIDS FROM OCTOCORALLIA .1. BIOACTIVE DITERPENOIDS - LITOPHYNOL-A AND LITOPHYNOL-B FROM THE MUCUS OF THE SOFT CORAL LITOPHYTON SP [J].
MIYAMOTO, T ;
YAMADA, K ;
IKEDA, N ;
KOMORI, T ;
HIGUCHI, R .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (09) :1212-1219
[10]   LITOPHYNIN-A AND LITOPHYNIN-B, 2 NEW INSECT GROWTH INHIBITORY DITERPENOIDS FROM THE SOFT CORAL LITOPHYTON SP [J].
OCHI, M ;
FUTATSUGI, K ;
KOTSUKI, H ;
ISHII, M ;
SHIBATA, K .
CHEMISTRY LETTERS, 1987, (11) :2207-2210