Synthetic approaches toward sesterterpenoids

Abstract

Sesterterpenoids account for many bioactive natural products, often with unusual and complex structural features, which makes them attractive targets for synthetic chemists. This review surveys efforts undertaken toward the synthesis of sesterterpenoids, focusing on completed total syntheses and covering ca. 50 natural products in total.

Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products

“…An excellent recent review by Trauner specifically covers this area of terpene research from a historic perspective. 380 …”

Enantioselective synthesis of an ophiobolin sesterterpene via a programmed radical cascade

“…Moreover, this work also represents one of the shortest total syntheses of any known sesterterpene natural product (40). In addition, this strategy represents a departure from biomimetic, cationic cascade processes in that the chiral reagent exerts its influence during the termination of the cascade, rather than its initiation (7); combinations of both may prove even more powerful.…”

Diastereoselective Synthesis of Isoindole‐Fused Diazacyclooctaindenones from Spiro­chromenes through Domino Reactions with Aliphatic 1,2‐Diamines

“…[1] Well over a hundred natural products containing eight-membered carbocycles have been isolated, and have become the targets of synthetic projects. [3,4] Target molecules containing eight-membered heterocycles have attracted extensive synthetic interest in recent years due to their presence in a large number of naturally occurring molecules, such as balasubramide (1), [5] serotobenine (2; Figure 1), [6] the lundurine class of molecules, [7] and 7-aza-(-)steganacin. [3,4] Target molecules containing eight-membered heterocycles have attracted extensive synthetic interest in recent years due to their presence in a large number of naturally occurring molecules, such as balasubramide (1), [5] serotobenine (2; Figure 1), [6] the lundurine class of molecules, [7] and 7-aza-(-)steganacin.…”

“…[3,4] Target molecules containing eight-membered heterocycles have attracted extensive synthetic interest in recent years due to their presence in a large number of naturally occurring molecules, such as balasubramide (1), [5] serotobenine (2; Figure 1), [6] the lundurine class of molecules, [7] and 7-aza-(-)steganacin. [9] Indole-fused eight-membered heterocycles are present in indole alkaloids such as deoxyisoaustamide (3) [10,11] (Figure 1) and the lundurines (namely, lundurine A). [9] Indole-fused eight-membered heterocycles are present in indole alkaloids such as deoxyisoaustamide (3) [10,11] (Figure 1) and the lundurines (namely, lundurine A).…”