Applications of Wittig Reaction in the Total Synthesis of Natural Macrolides

Abstract

The Wittig reaction involves the synthesis of an alkene via the conversion of an aldehyde or ketone with the already generated ylide from a phosphonium salt. Significantly, when this important name reaction is employed the desired alkenes are constructed via a predictable manner, thus resultant particularly are useful in the total synthesis of natural products and synthetic complex organic compounds with definite geometric isomers, exhibiting diverse biological potencies. In this review we try to highlight the applications of the Wittig reaction as an efficient and attractive strategy in the total synthesis of macrolides from 2008 to 2020.

Cинтез Нових Похідних Бензоксазину За Реакцією Віттіга

“…Головні переваги синтезу -утворення похідних алкенів із суворо визначеним розташуванням кратного зв'язку і високий вихід кінцевого продукту. Реакцію Віттіга до цього часу вважають найбільш ефективним способом отримання олефінів (Heravi et al, 2020).…”

“…Ukrainian Journal of Natural Sciences № 6 Український журнал природничих наук № 6 кінцевого продукту. Реакцію Віттіга до цього часу вважають найбільш ефективним способом отримання олефінів (Heravi et al, 2020).…”

High-speed Ball Milling Enables an Ultra-fast Wittig Olefination Under Ambient and Solvent-free Conditions Without Ylide Pre-formation

“…[3][4][5][6] Despite numerous adaptations, the classical Wittig reaction continues to be crucial in modern synthetic chemistry, with applications ranging from polymer chemistry [7][8][9] and material sciences 10,11 to drug and natural product synthesis. [12][13][14][15][16][17] Even on an industrial scale, the Wittig reaction is frequently pivotal; a prominent example is BASF's ton-scale synthesis of vitamin A and its derivatives. 5,[18][19][20][21][22][23] In light of growing environmental concerns, there is an urgent need for more sustainable and greener modifications of this widely used reaction.…”

Total synthesis of Oboflavanone B

“…At the very beginning, we tried to utilize Wittig reaction to break the double bond, however, the water produced during the ring-close reaction may affect the Wittig reagent. Herein, the double bond is transformed to a primary alcohol, and the elimination of the water to form a double bond requires a novel reaction which will be discussed in the forward synthesis section below [2,3]. After the ring-open step, the compound 2 is obtained (see Figure 3).…”