Record 6388   View: Standard Glossary  HistCite Guide
Author(s): Smith AB; Pitram SM
Title: Multicomponent linchpin couplings of silyl dithianes: Synthesis of the Schreiber C(16-28) trisacetonide subtarget for mycoticins A and B
Source: ORGANIC LETTERS 1 (12): 2001-2004
Date: 1999 DEC 16
Document Type: Journal : Article
DOI:  
Language: English
Comment:  
Address: Univ Penn, Dept Chem, Res Struct Matter Lab, Philadelphia, PA 19104 USA.
Univ Penn, Monell Chem Senses Ctr, Philadelphia, PA 19104 USA.
Reprint: Smith, AB, Univ Penn, Dept Chem, Res Struct Matter Lab, Philadelphia,
PA 19104 USA.
E-mail:  
Author Keywords:  
KeyWords Plus: MACROLIDE ANTIBIOTIC ROXATICIN; 2-DIRECTIONAL CHAIN SYNTHESIS; STEREOCHEMICAL ASSIGNMENT; 1,3-DIOL ACETONIDES; DIANION SYNTHON; POLYOL CHAINS; NMR ANALYSIS; 1,3-REARRANGEMENT; SPIROKETAL; STRATEGY
Abstract: [GRAPHICS] An efficient synthesis of trisacetonide (+)-11, the Schreiber C(16-28) subtarget for mycoticins A and a, is described. The key synthetic transformation entails a one-flask, five component linchpin coupling tactic.
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