TANDEM PERICYCLIC-REACTIONS (TPR) - A SIMPLE CONSTRUCTION OF FUNCTIONALIZED [3,N,1] BICYCLES AND A READY ENTRY INTO THE CORE OF GIBBERELLIC-ACID AND ZIZAENE

被引：32

作者：

MARKO, IE

SERES, P

EVANS, GR

SWARBRICK, TM

机构：

[1] Université Catholique de Louvain, Département de Chimie, Laboratoire de Chimie Organique, B-1348 Louvain-La-Neuve

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 45期

关键词：

D O I：

10.1016/S0040-4039(00)79315-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By combining our previously reported TPR methodology with an oxidative cleavage reaction, functionalised [3,n,1] bicycles can be produced in good yield. This methodology forms the basis of a simple approach towards the skeleton of gibberellic acid and the zizaenes.

引用

页码：7305 / 7308

页数：4

共 11 条

[1]

ANSELL MF, 1959, J CHEM SOC, P331

[2] TRITERPENOIDS .7. THE TRANSFORMATION OF LANOSTADIENOL (LANOSTEROL) INTO 14-METHYLCHOLESTAN-3-BETA-OL [J].

BARTON, DHR ;

IVES, DAJ ;

THOMAS, BR .

JOURNAL OF THE CHEMICAL SOCIETY, 1954, (MAR) :903-907

[3] INTRAMOLECULAR DIELS-ALDER REACTION WITH FURAN-DIENE .1. AN EXPEDITIOUS ENTRY INTO A FUNCTIONALIZED GIBBANE [J].

GROOTAERT, WM ;

DECLERCQ, PJ .

TETRAHEDRON LETTERS, 1982, 23 (32) :3291-3294

[4] THE CHEMISTRY OF GIBBERELLINS - AN OVERVIEW [J].

MANDER, LN .

CHEMICAL REVIEWS, 1992, 92 (04) :573-612

[5] TANDEM PERICYCLIC-REACTIONS - THE 1ST X-RAY STRUCTURE OF AN INITIAL PYRONE-OLEFIN ADDUCT AND AN EASY, STEREOCONTROLLED, ENTRY INTO POLYOXYGENATED CYCLOHEXANES [J].

MARKO, IE ;

SERES, P ;

SWARBRICK, TM ;

STATON, I ;

ADAMS, H .

TETRAHEDRON LETTERS, 1992, 33 (38) :5649-5652

[6] CONJUGATED KETENES - NEW ASPECTS OF THEIR SYNTHESIS AND SELECTED UTILITY FOR THE SYNTHESIS OF PHENOLS, HYDROQUINONES, AND QUINONES [J].

MOORE, HW ;

DECKER, OHW .

CHEMICAL REVIEWS, 1986, 86 (05) :821-830

[7] [2,3]-WITTIG SIGMATROPIC REARRANGEMENTS IN ORGANIC-SYNTHESIS [J].

NAKAI, T ;

MIKAMI, K .

CHEMICAL REVIEWS, 1986, 86 (05) :885-902

[8] OSMIUM TETROXIDE-CATALYZED PERIODATE OXIDATION OF OLEFINIC BONDS [J].

PAPPO, R ;

ALLEN, DS ;

LEMIEUX, RU ;

JOHNSON, WS .

JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (04) :478-479

[9]

PATTENDEN G, 1983, J CHEM SOC P1, P1901

[10] TANDEM PERICYCLIC-REACTIONS - NOVEL AND EFFICIENT METHODOLOGY FOR THE RAPID ASSEMBLY OF COMPLEX POLYCYCLIC SYSTEMS [J].

SWARBRICK, TM ;

MARKO, IE ;

KENNARD, L .

TETRAHEDRON LETTERS, 1991, 32 (22) :2549-2552

← 1 2 →