A general approach to 1,6,7-trihydroxyindolizidin-8-carboxylates is illustrated through the synthesis of a c-lactone in an enantiopure form in seven steps starting from (3S)-3-t-butyloxy-1-pyrroline N-oxide and the acetonide of (2E,4S)-4,5-dihydroxy-2- pentenoic acid derived from (S)-malic acid and mannitol, respectively. The process was completely stereoselective and allowed the total control of the relative and absolute configuration of the five contiguous stereocentres of the product.
Stereoselective synthesis of a new trihydroxyindolizidine lactone / F. PISANESCHI; M. PIACENTI; F. M. CORDERO; A. BRANDI. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - STAMPA. - 17:(2006), pp. 292-296. [10.1016/j.tetasy.2005.12.003]
Stereoselective synthesis of a new trihydroxyindolizidine lactone
CORDERO, FRANCA MARIA;BRANDI, ALBERTO
2006
Abstract
A general approach to 1,6,7-trihydroxyindolizidin-8-carboxylates is illustrated through the synthesis of a c-lactone in an enantiopure form in seven steps starting from (3S)-3-t-butyloxy-1-pyrroline N-oxide and the acetonide of (2E,4S)-4,5-dihydroxy-2- pentenoic acid derived from (S)-malic acid and mannitol, respectively. The process was completely stereoselective and allowed the total control of the relative and absolute configuration of the five contiguous stereocentres of the product.File | Dimensione | Formato | |
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