CONVENIENT AND SHORT ROUTE TO A KEY INTERMEDIATE IN THE SYNTHESIS OF FORSKOLIN

被引:3
作者
BACIGALUPPO, JA [1 ]
COLOMBO, MI [1 ]
ZINCZUK, J [1 ]
HUBER, SN [1 ]
MISCHNE, MP [1 ]
RUVEDA, EA [1 ]
机构
[1] UNIV NACL ROSARIO,CONSEJO NACL INVEST CIENT & TECN,FAC CIENCIAS BIOQUIM & FARMACEUT,RA-2000 ROSARIO,ARGENTINA
关键词
D O I
10.1080/00397919108021283
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The intermediate 2, previously used in several synthetic sequences toward forskolin (1), has been synthesized from enone 3. The key step in the sequence is the 1,3-oxidative rearrangement of the tertiary alcohol 5, which allowed the easy introduction of the keto group at C-6 of 2.
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页码:1361 / 1367
页数:7
相关论文
共 22 条
[1]   A NEW SYNTHETIC ROUTE TO (+/-)-FORSKOLIN [J].
BEGLEY, MJ ;
CHESHIRE, DR ;
HARRISON, T ;
HUTCHINSON, JH ;
MYERS, PL ;
PATTENDEN, G .
TETRAHEDRON, 1989, 45 (16) :5215-5246
[2]  
BHAT S V, 1977, Tetrahedron Letters, V19, P1669
[3]   SYNTHESIS OF THE ZIEGLER KEY INTERMEDIATE AND RELATED PRECURSORS FOR THE SYNTHESIS OF FORSKOLIN AND ERIGEROL [J].
COLOMBO, MI ;
ZINCZUK, J ;
BACIGALUPPO, JA ;
SOMOZA, C ;
RUVEDA, EA .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (21) :5631-5639
[4]   A SHORT AND EFFICIENT ENANTIOSELECTIVE ROUTE TO A KEY INTERMEDIATE FOR THE TOTAL SYNTHESIS OF FORSKOLIN [J].
COREY, EJ ;
JARDINE, PD .
TETRAHEDRON LETTERS, 1989, 30 (52) :7297-7300
[5]   TOTAL SYNTHESIS OF (+/-)-FORSKOLIN [J].
COREY, EJ ;
JARDINE, PD ;
ROHLOFF, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3672-3673
[6]   TOTAL SYNTHESIS OF A C-15 GINKGOLIDE, (+/-)-BILOBALIDE [J].
COREY, EJ ;
SU, WG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (24) :7534-7536
[7]   DIRECT OXIDATION OF TERTIARY ALLYLIC ALCOHOLS - SIMPLE AND EFFECTIVE METHOD FOR ALKYLATIVE CARBONYL TRANSPOSITION [J].
DAUBEN, WG ;
MICHNO, DM .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (04) :682-685
[8]   OPTICAL ROTATORY DISPERSION STUDIES .89. OCTANT RULE + T-BUTYL GROUP . SYNTHESIS OF STEROIDAL T-BUTYL KETONES [J].
DJERASSI, C ;
WARAWA, EJ ;
HART, PA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (01) :78-&
[9]  
GRIECO PA, 1978, TETRAHEDRON LETT, V20, P419
[10]   SYNTHESIS OF (-)-(R)-4-HYDROXY-BETA-IONONE AND (-)-(5R,6S)-5-HYDROXY-4,5-DIHYDRO-ALPHA-IONONE FROM (-)-(S)-ALPHA-IONONE [J].
HAAG, A ;
ESCHENMOSER, W ;
EUGSTER, CH .
HELVETICA CHIMICA ACTA, 1980, 63 (01) :10-15