The Preparation of (-)-Grandisine B from (+)-Grandisine D; A Biomimetic Total Synthesis or Formation of an Isolation Artefact?

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An efficient new alkyne-acetal cyclization procedure has been developed to prepare enantiopure Indolizidine building blocks from L-proline and then applied to prepare the Elaeocarpus-derived alkaloids grandisine B and grandisine D in an efficient manner. However, evidence Is presented which indicates that grandisine B does not occur naturally but is formed by reaction of grandisine D with ammonia during the extraction/purification process.

Original languageEnglish
Pages (from-to)3976-3979
Number of pages4
JournalOrganic Letters
Issue number15
Publication statusPublished - 5 Aug 2011

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