Asymmetric synthesis. XXII. Formal synthesis of (-)-perhydrohistrionicotoxin
The synthesis of (-)-depentylperhydrohistrionicotoxin (I, R = H) from the 2-cyano-6-oxazolopiperidine synthon (-)-II was achieved. The spiro skeleton was formed by an aldol cyclization of a Me ketone and an aldehyde function belonging to chains borne at C-2. Since the transformation of (+-)-I (R = H) into (+-)-perhydrohistrionicotoxin (I, R = pentyl) is known, the synthesis of (-)-I (R = H) represents a formal synthesis of (-)-perhydrohistrionicotoxin. [on SciFinder (R)]
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Zhu, J., Royer, J., Quirion, J. C., & Husson, H. P. (1991). Asymmetric synthesis. XXII. Formal synthesis of (-)-perhydrohistrionicotoxin. Tetrahedron Letters, 32(22), 2485–2488. https://doi.org/10.1016/S0040-4039(00)74361-9
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1991
32
22
2485
8
CAN 115:92664
31-3
Alkaloids
Inst. Chim. Subst. Nat.,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
82042-18-0P ((-)-Depentylperhydrohistrionicotoxin) Role: SPN (Synthetic preparation), PREP (Preparation) (asym. synthesis of); 40709-29-3P ((-)-Perhydrohistrionicotoxin) Role: RCT (Reactant), PREP (Preparation), RACT (Reactant or reagent) (formal asym. synthesis of); 135384-11-1P; 135384-17-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and Swern oxidn. of); 135500-40-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and alkylation of, with Bu lithium); 135500-42-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and debenzylation of); 135384-14-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and dehydration of); 135500-41-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydroboration-oxidn. of); 135384-13-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrogenation of); 135384-08-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrolysis of); 135384-12-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and intramol. cyclization of); 127708-18-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and methylation of); 135384-09-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and redn. of); 135500-43-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 135384-10-0P; 135500-44-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn., hydrogenolysis, and benzylation of); 88056-92-2 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with (bromoethyl)dioxolane); 18742-02-4 (2-(2-Bromoethyl)-1,3-dioxolane) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with cyanophenyloxazolopiperidine)
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