A Total Synthesis of ( + )‐2′S, 3′R‐Zoapatanol

Abstract

Three palladium‐catalyzed steps (allyl alkylation, Wacker oxidation, and carbonylative cross‐coupling) characterize the first asymmetric total synthesis of 1, a component of plant extracts used as contraceptives.

1,3-Dipolar cycloaddition reactions of nitrile oxides in the synthesis of natural compounds and their analogues

“…124 Syntheses of racemic zoapatanol 125,126 and the optically active product (Scheme 2) have been described. 127 D-Glucose diacetonide (120) was used as the starting compound in the 13-step synthesis of the oxime 121. The intramolecular nitrile oxide cycloaddition reaction was carried out under standard conditions.…”

Stereoselective Synthesis of Cyclic Ethers via the Palladium-Catalyzed Intramolecular Addition of Alcohols to Phosphono Allylic Carbonates

“…The ring size preference is 5>6>7 and primary, secondary, and tertiary alcohols were all viable nucleophiles 13. There are several examples of the cyclization of more complex substrates in natural product synthesis 14. In particular, Burke demonstrated an elegant use of the Trost ligand in the cyclo desymmetrization of diols and tetraols 15.…”

A Unified Strategy for Enantioselective Total Synthesis of Cladiellin and Briarellin Diterpenes: Total Synthesis of Briarellins E and F and the Putative Structure of Alcyonin and Revision of Its Structure Assignment

“…Removal of the TIPS protecting group of 53 with n -Bu 4 NF gave diol 54 . Exposure of this intermediate to Tf 2 O and 2,6-lutidine72 delivered dioxatricycle 55 after 4 days at room temperature in yields ranging from 55–68%. Under these conditions, the ratio of intramolecular etherification to elimination was ∼ 6:1 ( 1 H NMR analysis).…”