Synthesis and reactivity of optically active spiroketals by ring-expansion of chromium carbene complex-derived cyclobutanones

被引：28

作者：

Bueno, AB ^{[1
]}

Hegedus, LS ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 03期

关键词：

D O I：

10.1021/jo971665v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photolysis of cyclic chromium alkoxycarbene complexes with an optically active ene-carbamate gave spirofused, optically active cyclobutanones. Baeyer-Villiger ring expansion followed by further functionalization gave optically active spiroketals. Photochemical ring expansion of these spirofused cyclobutanones in the presence of acetic acid or thiophenol gave 2-acetoxy- or 2-(thiophenoxy)-4-spirofused tetrahydrofurans. Elimination of the thiophenoxy group gave a 3,4-dihydrofuran that underwent Heck arylation and photochemical cycloaddition with chromium carbene complexes to give cyclobutanones.

引用

页码：684 / 690

页数：7

共 34 条

[1]

ATKINS KE, 1970, TETRAHEDRON LETT, P3821

[2] Preparation of substituted indolines via anionic cyclization [J].

Bailey, WF ;

Jiang, XL .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08) :2596-2597

[3] Synthesis, resolution, and determination of absolute configuration of a vaulted 2,2'-binaphthol and a vaulted 3,3'-biphenanthrol (VAPOL) [J].

Bao, JM ;

Wulff, WD ;

Dominy, JB ;

Fumo, MJ ;

Grant, EB ;

Rob, AC ;

Whitcomb, MC ;

Yeung, SM ;

Ostrander, RL ;

Rheingold, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (14) :3392-3405

[4] SYNTHESIS OF AZAPENAMS, DIAZEPINONES, AND DIOXOCYCLAMS VIA THE PHOTOLYTIC REACTION OF CHROMIUM ALKOXYCARBENE COMPLEXES WITH IMIDAZOLINES [J].

BETSCHART, C ;

HEGEDUS, LS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5010-5017

[5] AN EFFICIENT AND STEREOSPECIFIC SYNTHESIS OF NOVEL PYRAZINE C-NUCLEOSIDES [J].

CHEN, JJ ;

WALKER, JA ;

LIU, WM ;

WISE, DS ;

TOWNSEND, LB .

TETRAHEDRON LETTERS, 1995, 36 (46) :8363-8366

[6] TOTAL SYNTHESIS OF +/-N-METHYLMAYSENINE [J].

COREY, EJ ;

WEIGEL, LO ;

FLOYD, D ;

BOCK, MG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (09) :2916-2918

[7] THE TOTAL SYNTHESIS OF AVERMECTIN-A1A [J].

DANISHEFSKY, SJ ;

ARMISTEAD, DM ;

WINCOTT, FE ;

SELNICK, HG ;

HUNGATE, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) :2967-2980

[8] A NOVEL METHOD FOR THE SYNTHESIS OF SPIROKETAL SYSTEMS - SYNTHESIS OF THE PHEROMONES OF THE COMMON WASP AND THE OLIVE FRUIT-FLY [J].

DESHONG, P ;

RYBCZYNSKI, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (10) :3207-3210

[9] 2-OXAZOLIDONES [J].

DYEN, ME ;

SWERN, D .

CHEMICAL REVIEWS, 1967, 67 (02) :197-&

[10] THE ASYMMETRIC-SYNTHESIS OF BETA-LACTAM ANTIBIOTICS .1. APPLICATION OF CHIRAL OXAZOLIDONES IN THE STAUDINGER REACTION [J].

EVANS, DA ;

SJOGREN, EB .

TETRAHEDRON LETTERS, 1985, 26 (32) :3783-3786

← 1 2 3 4 →