A concise synthesis of (-)-dihydrospirotryprostatin B via tandem Michael addition

Tetrahedron Letters
2021.0

Abstract

The asymmetric synthesis of (-)-dihydrospirotryprostatin B (3), a cytostatic spiro[pyrrolidine-3, 3'-oxindole] alkaloid, has been accomplished in 8 longest linear steps (LLS) from commercially available amino acids. The key step of the synthetic approach consists of the tandem Michael addition of oxindole derived from dipeptide diketopiperazine to alkynone, leading to the rapid construction of the spiro [pyrrolidine-3,3'-oxindole] scaffold with the consecutive quaternary spiro carbon center and chiral tertiary amine being diastereoselectively established. (C) 2021 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2021.153486

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