Total syntheses of Prelactone V and Prelactone B

S Raghavendra; Krishnaji Tadiparthi; J S Yadav

doi:10.1016/j.carres.2017.02.008

Total syntheses of Prelactone V and Prelactone B

Carbohydr Res. 2017 Apr 10:442:17-19. doi: 10.1016/j.carres.2017.02.008. Epub 2017 Feb 28.

Authors

S Raghavendra¹, Krishnaji Tadiparthi², J S Yadav³

Affiliations

¹ Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad, 500007, India; Dept. of Pharmaceutical Chemistry, School of Pharmacy and Health Sciences, International Medical University, Kuala Lumpur, 57000, Malaysia. Electronic address: srgoud2@gmail.com.
² Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad, 500007, India; Department of Chemistry, Christ University, Hosur Road, Bangalore, 560029, India.
³ Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad, 500007, India.

PMID: 28282511
DOI: 10.1016/j.carres.2017.02.008

Abstract

The total syntheses of natural products Prelactone-V and Prelactone-B have been accomplished by a novel Chiron approach starting from d-glucose. The synthesis involves isopropylidene acetal formation of d-glucose using Poly(4-vinylpyridine) supported iodine as a catalyst, Tebbe olefination, Grignard reaction, Wittig olefination, selective mono deprotection of acetal using PMA/SiO₂, hydrogenation and anti-1,3-diol formation are as key steps.

Keywords: Grignard reaction and Tebbe reaction; Lactonisation; P(4-VPI)(+)I(3)(−); PMA/SiO(2); Wittig olefination; d-glucose.

MeSH terms

Lactones / chemical synthesis*
Lactones / chemistry
Molecular Conformation

Substances

Lactones
prelactone B
prelactone V