Synthesis of crossed [2+2] photocycloadducts: A novel approach to the synthesis of bridged bicyclic alkenes

被引:30
作者
Crimmins, MT [1 ]
Hauser, EB [1 ]
机构
[1] Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
关键词
D O I
10.1021/ol991272d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A solution to the synthesis of "crossed" intramolecular [2 + 2] photocycloadducts has been achieved. Through the use of a temporary heteroatom linker, the equivalent of a crossed photocycloadduct can be accessed at the expensive of the normal "straight" adduct, Selectivity as high as 94:6 for the "crossed" adduct has been observed.
引用
收藏
页码:281 / 284
页数:4
相关论文
共 27 条
[1]   THE MECHANISM OF THE PHOTOCHEMICAL CYCLOADDITION REACTION BETWEEN 2-CYCLOPENTENONE AND POLAR ALKENES - TRAPPING OF TRIPLET 1,4-BIRADICAL INTERMEDIATES WITH HYDROGEN SELENIDE [J].
ANDREW, D ;
HASTINGS, DJ ;
WEEDON, AC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) :10870-10882
[2]  
[Anonymous], CHEM REV
[3]   Total synthesis of (±)-ginkgolide B [J].
Crimmins, MT ;
Pace, JM ;
Nantermet, PG ;
Kim-Meade, AS ;
Thomas, JB ;
Watterson, SH ;
Wagman, AS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (43) :10249-10250
[4]   ADDITION OF ZINC HOMOENOLATES TO ACETYLENIC ESTERS AND AMIDES - A FORMAL [3+2] CYCLOADDITION [J].
CRIMMINS, MT ;
NANTERMET, PG ;
TROTTER, BW ;
VALLIN, IM ;
WATSON, PS ;
MCKERLIE, LA ;
REINHOLD, TL ;
CHEUNG, AWH ;
STETSON, KA ;
DEDOPOULOU, D ;
GRAY, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1038-1047
[5]   SYNTHETIC STUDIES ON THE GINKGOLIDES - TOTAL SYNTHESIS OF (+/-)-BILOBALIDE [J].
CRIMMINS, MT ;
JUNG, DK ;
GRAY, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (08) :3146-3155
[6]   Asymmetric total synthesis of callystatin A: Asymmetric aldol additions with titanium enolates of acyloxazolidinethiones [J].
Crimmins, MT ;
King, BW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) :9084-9085
[7]   INTRAMOLECULAR PHOTOCYCLOADDITION - CYCLOBUTANE FRAGMENTATION - TOTAL SYNTHESIS OF (+/-)-LAURENENE [J].
CRIMMINS, MT ;
GOULD, LD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (20) :6199-6200
[8]   CP-225,917 and CP-263,114: Novel ras farnesylation inhibitors from an unidentified fungus .2. Structure elucidation [J].
Dabrah, TT ;
Kaneko, T ;
Massefski, W ;
Whipple, EB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (07) :1594-1598
[9]   FREE RADICAL-MEDIATED RING EXPANSION AND RELATED ANNULATIONS [J].
DOWD, P ;
ZHANG, W .
CHEMICAL REVIEWS, 1993, 93 (06) :2091-2115
[10]   SYNTHESIS OF NITROGEN-HETEROCYCLES VIA CATALYTIC RING-CLOSING METATHESIS OF DIENES [J].
FU, GC ;
GRUBBS, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (18) :7324-7325