ACETOXYFULVENE SYNTHESIS OF PROSTAGLANDINS .1. SYNTHESIS OF THE COREY ALDEHYDE

被引：32
作者：
BROWN, ED
CLARKSON, R
LEENEY, TJ
ROBINSON, GE
机构：
[1] I.C.I. Limited, Pharmaceuticals Division, Mereside, Macclesfield, Cheshire SK10 4TG, Alderley Park
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1978年 / 12期
关键词：
D O I：
10.1039/p19780001507
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A short and practical alternative synthesis of the Corey aldehyde (2), a key intermediate in prostaglandin synthesis, is described. 6-Acetoxyfulvene (7) underwent a Diels-Alder reaction with 2-chloroacrylonitrile to give 7-acetoxy-methylene-2-chlorobicyclo[2.2.1]hept-5-ene-2-carbonitrile (8) which was converted sequentially into 2-chloro-7-anti-formylbicyclo[2.2.1]hept-5-ene-2-carbonitrile (10) and its 7-syn-isomer (11). The factors controlling the stereochemistry at C(7) in the anti- and syn-aldehydes (10) and (11) are discussed in detail.
引用
收藏
页码：1507 / 1511
页数：5
相关论文
共 18 条
[1]   16-ARYLOXYPROSTAGLANDINS - NEW CLASS OF POTENT LUTEOLYTIC AGENT [J].
BINDER, D ;
BOWLER, J ;
BROWN, ED ;
CROSSLEY, NS ;
HUTTON, J ;
SENIOR, M ;
SLATER, L ;
WILKINSON, P ;
WRIGHT, NCA .
PROSTAGLANDINS & OTHER LIPID MEDIATORS, 1974, 6 (01) :87-90
[2]   ACETOXYFULVENE SYNTHESIS OF PROSTAGLANDINS - ALTERNATIVE SYNTHESIS OF COREY ALDEHYDE [J].
BROWN, ED ;
CLARKSON, R ;
LEENEY, TJ ;
ROBINSON, GE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (16) :642-642
[3]   RATES OF REACTION OF SODIUM BOROHYDRIDE WITH BICYCLIC KETONES STERIC APPROACH CONTROL AND STERIC DEPARTURE CONTROL IN REACTIONS OF RIGID BICYCLIC SYSTEMS [J].
BROWN, HC ;
MUZZIO, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (12) :2811-+
[4]  
Browning E, 1961, TOXICITY IND METALS
[5]   METHOXYMETHYLATION OF THALLOUS CYCLOPENTADIENIDE - SIMPLIFIED PREPARATION OF A KEY INTERMEDIATE FOR SYNTHESIS OF PROSTAGLANDINS [J].
COREY, EJ ;
KOELLIKER, U ;
NEUFFER, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (06) :1489-+
[6]   REAGENTS FOR STEREOSELECTIVE CARBONYL REDUCTION - IMPROVED SYNTHETIC ROUTE TO PRIMARY PROSTAGLANDINS [J].
COREY, EJ ;
ALBONICO, SM ;
KOELLIKER, U ;
SCHAAF, TK ;
VARMA, RK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (06) :1491-+
[7]   STEREO-CONTROLLED SYNTHESIS OF PROSTAGLANDINS F2ALPHA AND E2 (DL) [J].
COREY, EJ ;
WEINSHENKER, NM ;
SCHAAF, TK ;
HUBER, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (20) :5675-+
[8]   SYNTHESIS AND BIOLOGICAL-ACTIVITY OF POTENT, SELECTIVE, LUTEOLYTIC PROSTAGLANDINS [J].
CROSSLEY, NS .
PROSTAGLANDINS, 1975, 10 (01) :5-18
[9]   POTENT LUTEOLYTIC AGENTS RELATED TO PROSTAGLANDIN-F2ALPHA [J].
DUKES, M ;
RUSSELL, W ;
WALPOLE, AL .
NATURE, 1974, 250 (5464) :330-331
[10]  
FIESER LF, 1976, REAGENTS ORGANIC SYN, P146
12