First stereoselective synthesis of (1S,2S,4R,5R)-(−)-β-multistriatin

Starting from 2,3‐O‐(3‐pentylidene)‐D‐glyceraldehyde (3), we prepared the bicyclic pheromone (1S,2S,4R,5R)‐(−)‐β‐multistriatin (1) on a gram scale. Key steps of the synthesis are a cis‐selective Wittig olefination followed by diastereo‐selective Michael addition and hydrogenation....

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Veröffentlicht in:	Liebigs Annalen 1995-06, Vol.1995 (6), p.1011-1014
Hauptverfasser:	Henrichfreise, Peter, Scharf, Hans-Dieter
Format:	Artikel
Sprache:	eng
Schlagworte:	2,3‐O‐(3‐Pentylidene)‐D‐glyceraldehyde 3-O-(3-Pentylidene)-D-glyceraldehyde cis-selective diastereoselective Hydrogenation Hydrogenation, diastereoselective Michael reaction Michael reaction, diastereoselective Multistriatin Wittig Olefination Wittig Olefination, cis‐selective
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Beschreibung
Zusammenfassung:	Starting from 2,3‐O‐(3‐pentylidene)‐D‐glyceraldehyde (3), we prepared the bicyclic pheromone (1S,2S,4R,5R)‐(−)‐β‐multistriatin (1) on a gram scale. Key steps of the synthesis are a cis‐selective Wittig olefination followed by diastereo‐selective Michael addition and hydrogenation.
ISSN:	0947-3440 1099-0690
DOI:	10.1002/jlac.1995199506143