PMID- 21283562
OWN - NLM
STAT- PubMed-not-MEDLINE
DCOM- 20120824
LR  - 20211020
IS  - 1860-5397 (Electronic)
IS  - 1860-5397 (Linking)
VI  - 6
DP  - 2010 Dec 20
TI  - Bronsted acid-promoted azide-olefin [3 + 2] cycloadditions for the preparation of 
      contiguous aminopolyols: The importance of disiloxane ring size to a 
      diastereoselective, bidirectional approach to zwittermicin A.
PG  - 1206-10
LID - 10.3762/bjoc.6.138 [doi]
AB  - We report the first study of substrate-controlled diastereoselection in a double 
      [3 + 2] dipolar cycloaddition of benzyl azide with alpha,beta-unsaturated imides. Using 
      a strong Bronsted acid (triflic acid) to activate the electron deficient imide 
      pi-bond, high diastereoselection was observed provided that a 
      1,1,3,3-tetraisopropoxydisiloxanylidene group (TIPDS) is used to restrict the 
      conformation of the central 1,3-anti diol. This development provides a basis for 
      a stereocontrolled approach to the aminopolyol core of (-)-zwittermicin A using a 
      bidirectional synthesis strategy.
FAU - Muchalski, Hubert
AU  - Muchalski H
AD  - Vanderbilt University and Vanderbilt Institute of Chemical Biology, Nashville, TN 
      37235, United States.
FAU - Hong, Ki Bum
AU  - Hong KB
FAU - Johnston, Jeffrey N
AU  - Johnston JN
LA  - eng
PT  - Journal Article
DEP - 20101220
PL  - Germany
TA  - Beilstein J Org Chem
JT  - Beilstein journal of organic chemistry
JID - 101250746
PMC - PMC3028999
OTO - NOTNLM
OT  - TIPDS
OT  - azide
OT  - bidirectional synthesis
OT  - cycloaddition
OT  - dialkoxydisiloxane
OT  - triazoline
OT  - triflic acid
OT  - zwittermicin A
EDAT- 2011/02/02 06:00
MHDA- 2011/02/02 06:01
PMCR- 2010/12/20
CRDT- 2011/02/02 06:00
PHST- 2010/10/04 00:00 [received]
PHST- 2010/11/24 00:00 [accepted]
PHST- 2011/02/02 06:00 [entrez]
PHST- 2011/02/02 06:00 [pubmed]
PHST- 2011/02/02 06:01 [medline]
PHST- 2010/12/20 00:00 [pmc-release]
AID - 10.3762/bjoc.6.138 [doi]
PST - epublish
SO  - Beilstein J Org Chem. 2010 Dec 20;6:1206-10. doi: 10.3762/bjoc.6.138.