Improved procedure for the oxidative cleavage of olefins by OsO4-NaIO4

被引:401
作者
Yu, WS [1 ]
Mei, Y [1 ]
Kang, Y [1 ]
Hua, ZM [1 ]
Jin, ZD [1 ]
机构
[1] Univ Iowa, Coll Pharm, Div Med & Nat Prod Chem, Iowa City, IA 52242 USA
关键词
D O I
10.1021/ol0400342
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxidative cleavage of olefins by OsO4-NaIO4 Sometimes suffers from low yields due to the formation of side products. It is found that the addition of 2,6-lutidine can suppress the side reactions and dramatically improve the yield of this classic reaction.
引用
收藏
页码:3217 / 3219
页数:3
相关论文
共 9 条
[1]  
Criegee R, 1942, LIEBIGS ANN CHEM, V550, P99
[2]   RING-OPENING OF ACETAL-III (8,13/13,17-DIEPOXY-14,15-DINORLABDANE) AND THE SYNTHESIS OF POTENTIAL ODORANTS DERIVED FROM MANOOL [J].
GRANT, PK ;
HANTON, LR ;
LYNCH, GP ;
ROBINSON, WT ;
WONG, G .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (01) :71-90
[3]   ORIGIN OF EPSILON-HYDROXY KETONES IN THE OSMIUM TETROXIDE-CATALYZED ASYMMETRIC DIHYDROXYLATION OF ALKENES [J].
LOHRAY, BB ;
BHUSHAN, V ;
KUMAR, RK .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (06) :1375-1380
[4]   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
[5]  
RANCAVILLA C, 2003, ORG LETT, V5, P1233
[6]   Studies on the synthesis of bafilomycin A1:: Stereochemical aspects of the fragment assembly aldol reaction for construction of the C(13)-C(25) segment [J].
Roush, WR ;
Bannister, TD ;
Wendt, MD ;
Jablonowski, JA ;
Scheidt, KA .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12) :4275-4283
[7]   Conformation-activity relationships in polyketide natural products: A new perspective on the rational design of epothilone analogues [J].
Taylor, RE ;
Chen, Y ;
Beatty, A ;
Myles, DC ;
Zhou, YQ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (01) :26-27
[8]   Synthesis of the middle fragment of oxazolomycin [J].
Wang, ZY ;
Moloney, MG .
TETRAHEDRON LETTERS, 2002, 43 (52) :9629-9632
[9]   Synthetic studies of antitumor natural products superstolides A and B. Construction of C20-C26 fragment of superstolide A [J].
Yu, WS ;
Zhang, Y ;
Jin, ZD .
ORGANIC LETTERS, 2001, 3 (10) :1447-1450