Use of conjugated dienones in cyclialkylations: Total syntheses of arucadiol, 1,2-didehydromiltirone, (+/-)-hinokione, (+/-)-nimbidiol, sageone, and miltirone

被引:53
作者
Majetich, G
Liu, S
Fang, J
Siesel, D
Zhang, Y
机构
[1] Department of Chemistry, University of Georgia, Athens
关键词
D O I
10.1021/jo970570q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Functionalized hydrophenanthrenes can be prepared using a cyclialkylation-based strategy. These annulations are highly dependent on the directing effects of the arene substitutents and on conformational considerations. The utility of this methodology was featured in the syntheses of six diterpenoids.
引用
收藏
页码:6928 / 6951
页数:24
相关论文
共 49 条
[1]   APPROACHES TO SYNTHESIS OF TRITERPENOIDS .2. SOME TETRACYCLIC PRECURSORS SUITABLE FOR CONVERSION INTO PENTACYCLIC TRITERPENOIDS [J].
APSIMON, JW ;
BUCCINI, J ;
BAKER, P ;
MACAULAY, S ;
HOOPER, JW .
CANADIAN JOURNAL OF CHEMISTRY, 1972, 50 (12) :1944-&
[2]   SYNTHESIS OF CYCLOHEXENONES [J].
BORN, H ;
PAPPO, R ;
SZMUSZKOVICZ, J .
JOURNAL OF THE CHEMICAL SOCIETY, 1953, (JUN) :1779-1782
[3]  
BRUNSON HA, 1940, J AM CHEM SOC, V62, P36
[4]   SYNTHESIS OF ALKENES FROM CARBONYL-COMPOUNDS AND CARBANIONS-ALPHA TO SILICON .6. SYNTHESIS OF TERMINAL ALLENES AND ALLYL CHLORIDES [J].
CHAN, TH ;
MYCHAJLOWSKIJ, W ;
ONG, BS ;
HARPP, DN .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (08) :1526-1532
[5]   STRUCTURE ELUCIDATION AND TOTAL SYNTHESIS OF NEW TANSHINONES ISOLATED FROM SALVIA-MILTIORRHIZA BUNGE (DANSHEN) [J].
CHANG, HM ;
CHENG, KP ;
CHOANG, TF ;
CHOW, HF ;
CHUI, KY ;
HON, PM ;
TAN, FWL ;
YANG, Y ;
ZHONG, ZP ;
LEE, CM ;
SHAM, HL ;
CHAN, CF ;
CUI, YX ;
WONG, HNC .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3537-3543
[6]  
CHANG HM, 1986, PHARM APPLICATIONS C, V1, P255
[7]   The condensation of aldehyde with ammonia to pyridin bases [J].
Tschitschibabin, AE .
JOURNAL FUR PRAKTISCHE CHEMIE-LEIPZIG, 1924, 107 (1/4) :122-128
[8]   SYNTHESIS OF 15-DEOXY-16-BETA-ETHOXYBRUCEANTIN AND SYNTHETIC EFFORTS TOWARD BRUCEANTIN [J].
CHIU, CKF ;
GOVINDAN, SV ;
FUCHS, PL .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (02) :311-323
[9]   THE SYNTHESIS OF DL-HINOKIONE METHYL ETHER [J].
CHOW, YL .
ACTA CHEMICA SCANDINAVICA, 1960, 14 (07) :1671-1672
[10]   OVERCROWDED MOLECULES .16. THERMAL AND PHOTO-CHEMICAL REACTIONS OF (E,E)-BIS(BENZYLIDENE)SUCCINIC ANHYDRIDE [J].
CRESCENTE, O ;
HELLER, HG ;
OLIVER, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (01) :150-153