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

TY - JOUR

T1 - The Preparation of (-)-Grandisine B from (+)-Grandisine D; A Biomimetic Total Synthesis or Formation of an Isolation Artefact?

AU - Cuthbertson, James D.

AU - Godfrey, Andrew A.

AU - Taylor, Richard J. K.

PY - 2011/8/5

Y1 - 2011/8/5

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=79961082227&partnerID=8YFLogxK

U2 - 10.1021/ol2014939

DO - 10.1021/ol2014939

M3 - Article

SN - 1523-7060

VL - 13

SP - 3976

EP - 3979

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -