title: Organocatalytic 1,4-conjugate addition of ascorbic acid to α,β-unsaturated aldehydes: bio-inspired total syntheses of leucodrin, leudrin and proposed structure of dilaspirolactone.
abstract: The organocatalytic additions of ascorbic acid to various α,β-unsaturated aldehydes via tandem 1,4-conjugate addition/hemiacetalization/hemiketalization were developed, which provided a rapid entry into the 5-5-5 spirodilactone cores of a family of ascorbylated natural products. Based on the described chemistry, total syntheses of leucodrin, leudrin and the proposed structure of dilaspirolactone were achieved.
authors: The Comprehensive AIDS Research Center, Department of Pharmacology and Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084, China.
authors: Zhaofeng
authors: Z
authors: Wang
authors: Kun
authors: K
authors: Zhao
authors: Junkai
authors: J
authors: Fu
authors: Junlin
authors: J
authors: Zhang
authors: Weiyu
authors: W
authors: Yin
authors: Yefeng
authors: Y
authors: Tang
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001205:Ascorbic Acid / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013148:Spironolactone / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D007783:Lactones; D013141:Spiro Compounds; C584206:leudrin; D013148:Spironolactone; C584205:leucodrin; D001205:Ascorbic Acid