Total Synthesis of Leucascandrolide A: A New Application of the Mukaiyama Aldol−Prins Reaction

A total synthesis of the marine natural product leucascandrolide A has been completed. The titanium tetrabromide-mediated Mukaiyama aldol−Prins (MAP) reaction with aldehydes developed in our group provided a highly convergent and stereoselective method for assembling the core of the molecule. A new...

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Veröffentlicht in:	Journal of organic chemistry 2007-07, Vol.72 (15), p.5784-5793
Hauptverfasser:	Van Orden, Lori J, Patterson, Brian D, Rychnovsky, Scott D
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Kinetics and mechanisms Magnetic Resonance Spectroscopy Organic chemistry Oxazoles - chemistry Preparations and properties Reactivity and mechanisms Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Spectrometry, Mass, Electrospray Ionization
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container_end_page	5793
container_issue	15
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container_title	Journal of organic chemistry
container_volume	72
creator	Van Orden, Lori J Patterson, Brian D Rychnovsky, Scott D
description	A total synthesis of the marine natural product leucascandrolide A has been completed. The titanium tetrabromide-mediated Mukaiyama aldol−Prins (MAP) reaction with aldehydes developed in our group provided a highly convergent and stereoselective method for assembling the core of the molecule. A new class of MAP reactions with acetals is introduced, and mechanistic considerations for both MAP methods are described. The total synthesis was completed by coupling of the side chain through two avenues: a known Still−Gennari olefination and a new Z-selective aldol/dehydroselenation reaction. Both procedures were highly selective and provided the natural product.
doi_str_mv	10.1021/jo070901r
format	Article
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Org. Chem</addtitle><date>2007-07-20</date><risdate>2007</risdate><volume>72</volume><issue>15</issue><spage>5784</spage><epage>5793</epage><pages>5784-5793</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A total synthesis of the marine natural product leucascandrolide A has been completed. The titanium tetrabromide-mediated Mukaiyama aldol−Prins (MAP) reaction with aldehydes developed in our group provided a highly convergent and stereoselective method for assembling the core of the molecule. A new class of MAP reactions with acetals is introduced, and mechanistic considerations for both MAP methods are described. The total synthesis was completed by coupling of the side chain through two avenues: a known Still−Gennari olefination and a new Z-selective aldol/dehydroselenation reaction. 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source	MEDLINE; American Chemical Society Journals
subjects	Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Kinetics and mechanisms Magnetic Resonance Spectroscopy Organic chemistry Oxazoles - chemistry Preparations and properties Reactivity and mechanisms Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Spectrometry, Mass, Electrospray Ionization
title	Total Synthesis of Leucascandrolide A: A New Application of the Mukaiyama Aldol−Prins Reaction
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