274262-64-5

Upstream product

• 873956-12-8 4-(2'-benzyloxyethyl)-7aR-ethyl-1,2,3,6,7,7a-hexahydroinden-5-one 
• 197523-39-0 6-(benzyloxy)hex-1-en-3-one 
• 126260-80-8 (3RS)-6-benzyloxyhex-1-en-3-ol 

Downstream Products

• 7013-58-3 (+)-aspidospermidine 
• 4724-62-3 (3¹S,6aR,9aR)-6a-ethyloctahydro-1H-pyrrolo[3,2,1-ij]quinolin-9(2H)-one 
• 274262-65-6 C₂₅H₃₆O₄ 

Relevant academic research and scientific papers

Revisiting a classic approach to the Aspidosperma alkaloids: An intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine

A total synthesis of (+)-aspidospermidine (1) is described. The key reactions used in the synthesis of this pentacyclic Aspidosperma alkaloid were a deracemizing imine alkylation/Robinson annulation sequence, a selective "redox ketalization", and an intramolecular Schmidt reaction. A Fischer indolization step carried out on a tricyclic ketone mirrored the sequence reported by Stork and Dolfini in their classic aspidospermine synthesis.

Regiocontrol in an Intramolecular Schmidt Reaction: Total Synthesis of (+)-Aspidospermidine

(Matrix Presented) A total synthesis of (+)-aspidospermidine (1) is described, featuring an intramolecular Schmidt reaction as the key step. The effects of stereochemistry and protecting group status on the regio- and chemoselectivity of this reaction were examined.