Rearrangement of Freelingyne with Base

Abstract

Treatment of freelingyne (1) with sodium hydroxide in aqueous methanol gives the rearranged acid (2a).

Microthecaline A, a Quinoline Serrulatane Alkaloid from the Roots of the Australian Desert Plant Eremophila microtheca

“…This species then undergoes aromatization to form the intermediate (vii), an enantiomer of a brown algal natural product, erogorgiaene. 22,23 Following oxidation of erogorgiaene, the plant natural product 5,8-dihydroxyserrulat-14-en-18-al 24 (viii) is formed. The second stage of the proposed biosynthesis is not well understood; however it may be postulated that the introduction of a nitrogen atom (via an amino acid 25,26 ) results in the ring closure that leads to a quinoline moiety and thus the formation of microthecaline A (1).…”

The interaction of homophthalic anhydride with (triphenylphosphoranylidene)acetates

“…Acylation of ylide 2a with AHPA 1 was performed in Wittig reaction conditions proposed in publications [2,4]. However, we Acid 4 is formed by base-catalysed selfcondensation of AHPA that is well-known in AHPA chemistry [5][6][7][8].…”

Selective Reduction of Serrulatenol as a Route to Seco-Pseudopterosin Analogues

“…Serrulatenol is the only serrulatane reported which allows access to the 5,8-dioxygenated substitution pattern in contrast with the 7,8 pattern found in the aglycone of the seco-pseudopterosins. The stereochemistry of serrulatenol has been confirmed by X-ray analysis (8). The present problem, which involves conversion of serrulatenol {3} into 5,8-dimethyoxyserrulatane [12], essentially requires deoxygenation at C-13 and C-18 without isomerization at C-11.…”

“…The serrulatenol used in this study was part of a sample whose structure has been confirmed by Xray crystallography (8).…”