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Enantioselective Synthesis of (+)-Peganumine A

Enantioselective Synthesis of (+)-Peganumine A

Cyril Piemontesi, Qian Wang, Jieping Zhu

J Am Chem Soc. 2016 Sep 7;138(35):11148-51.

PMID: 27558528

Abstract:

A gram-scale enantioselective total synthesis of (+)-peganumine A was accomplished in 7 steps from commercially available 6-methoxytryptamine. Key steps included (a) a Liebeskind-Srogl cross-coupling; (b) a one-pot construction of the tetracyclic skeleton from an ω-isocyano-γ-oxo-aldehyde via a sequence of an unprecedented C-C bond forming lactamization and a transannular condensation; (c) a one-pot organocatalytic process merging two achiral building blocks into an octacyclic structure via a sequence of enantioselective Pictet-Spengler reaction followed by a transannular cyclization. This last reaction created two spirocycles and a 2,7-diazabicyclo[2.2.1]heptan-3-one unit with excellent control of both the absolute and relative stereochemistry of the two newly created quaternary stereocenters.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP3610364	6-Methoxytryptamine		3610-36-4	Price

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