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1.
Chem Sci ; 15(19): 7300-7307, 2024 May 15.
Article in English | MEDLINE | ID: mdl-38756805

ABSTRACT

Enantioselective construction of small molecules displaying a configurationally stable helical shape built on a fused-tetracyclic core is a daunting synthetic challenge even more pronounced when five-membered rings are incorporated in the structure. The resulting higher configurational lability strongly hampers their access, and therefore the development of new efficient methodologies is timely and highly desirable. In this context, we describe a padlocking approach via the enantioselective organocatalytic domino furannulation of appropriately designed achiral fused-tricyclic precursors resulting in the synthesis of configurationally locked helically chiral tetracyclic scaffolds featuring one or two five-membered rings with the simultaneous control of central and helical chiralities.

2.
J Org Chem ; 87(22): 15713-15718, 2022 11 18.
Article in English | MEDLINE | ID: mdl-36349937

ABSTRACT

Polygonapholine was isolated in 1997 from the Polygonatum alte-lobatum rhizome. Based on spectroscopic data, it was assigned a structure comprising an unusual cis-2,6-disubstituted bis-aryl morpholine ring to which is attached a (Z)-4-hydroxycinnamate as an amide and an (E)-4-hydroxycinnamate as an ester. Being a meso compound, polygonapholine should not exhibit an optical rotation as reported. A total synthesis of the purported morpholine alkaloid presented herein reveals discrepancies between the synthetic and the natural product casting doubt on the originally proposed structure.


Subject(s)
Alkaloids , Biological Products , Rhizome/chemistry , Spectrum Analysis , Morpholines , Molecular Structure
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