INTRAMOLECULAR DIELS-ALDER ADDITIONS TO 2-BENZOPYRAN-8-ONES - ANTI-SELECTIVITY INDUCED BY THE PHENYLSULFONYL GROUP

被引：6

作者：

BUSH, EJ

JONES, DW

NONGRUM, FM

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1994年 / 18期

关键词：

D O I：

10.1039/c39940002145

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The 2-benzopyran-3-ones 7a and 7c undergo intramolecular Diels-Alder addition via preferred endo-addition of the connecting chain, whereas for 7d and 7e (X = SO(2)Ph), exo-addition of the chain is preferred; the main adducts from the tatter additions (9d and 9e), give the diterpene-related products 12 (R = H, Y = OMe) and 12 (R = Me, Y = OMe) upon treatment with sodium amalgam.

引用

收藏

页码：2145 / 2146

页数：2

相关论文

共 14 条

[1] 2-BENZOPYRAN-3-ONES AS SYNTHETIC BUILDING-BLOCKS - REGIOSELECTIVE DIELS-ALDER ADDITIONS WITH SIMPLE OLEFINS LEADING TO AROMATIC STEROIDS [J].

BLEASDALE, DA ;

JONES, DW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (07) :1683-1692

[2] ASYMMETRIC TOTAL SYNTHESIS OF (-)-PODOPHYLLOTOXIN [J].

BUSH, EJ ;

JONES, DW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (15) :1200-1201

[3]

CIGANEK E, 1984, ORG REACTIONS, V32, P37

[4] INTRAMOLECULAR DIELS-ALDER REACTIONS OF SULFONYL-SUBSTITUTED TRIENES [J].

CRAIG, D ;

FISCHER, DA ;

KEMAL, O ;

MARSH, A ;

PLESSNER, T ;

SLAWIN, AMZ ;

WILLIAMS, DJ .

TETRAHEDRON, 1991, 47 (18-19) :3095-3128

[5] THERMAL, PHOTOCHEMICAL, AND TRANSITION-METAL MEDIATED ROUTES TO STEROIDS BY INTRAMOLECULAR DIELS-ALDER REACTIONS OF ORTHO-XYLYLENES (ORTHO-QUINODIMETHANES) [J].

FUNK, RL ;

VOLLHARDT, KPC .

CHEMICAL SOCIETY REVIEWS, 1980, 9 (01) :41-61

[6] A CONCISE BIOMIMETIC TOTAL SYNTHESIS OF (+/-)-TAXODIONE VIA A BF3.MENO2 PROMOTED CATIONIC CASCADE ANNULATION [J].

HARRING, SR ;

LIVINGHOUSE, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (06) :502-503

[7] SYNTHESIS OF ANTHRACYCLINONES VIA ORTHO-QUINONOID PYRONES [J].

JONES, DW ;

LOCK, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (21) :1509-1510

[8] O-QUINONOID COMPOUNDS .10. ENDO-SELECTIVITY IN DIELS-ALDER ADDITIONS OF NON-CONJUGATED OLEFINS TO O-QUINODIMETHANES [J].

JONES, DW ;

KNEEN, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (15) :1647-1654

[9] SYNTHESIS OF (+/-)-PISIFERIN, (+/-)-PISIFEROL, AND RELATED-COMPOUNDS BY INTRAMOLECULAR [4 + 2]CYCLOADDITION [J].

KAMETANI, T ;

KONDOH, H ;

TSUBUKI, M ;

HONDA, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (01) :5-10

[10] CHEMICAL EVIDENCE FOR THE PARTICIPATION OF A PEREPOXIDE INTERMEDIATE IN THE REACTION OF SINGLET OXYGEN WITH MONO-OLEFINS IN RELATIONSHIP WITH THE BIOGENETIC PATHWAY TO HIGHLY OXIDIZED ABIETANE DITERPENES [J].

LUIS, JG ;

ANDRES, LS ;

FLETCHER, WQ .

TETRAHEDRON LETTERS, 1994, 35 (01) :179-182