Enantioselective total synthesis of (−)-pseudophrynaminol through tandem olefination, isomerization and asymmetric Claisen rearrangement

Structure, Bioactivity and Synthesis of Natural Products with Hexahydropyrrolo[2,3‐b]indole

“…[194,195] The process comprises olefination, isomerization, Claisen rearrangement, and deacetylation to give 3-allyl-3-cyanomethylindolin-2-ones of the type 178.…”

Enantioselective total synthesis of (−)-flustramines A, B and (−)-flustramides A, B via domino olefination/isomerization/Claisen rearrangement sequence

“…14 Recently we have evolved our synthetic methodology using the domino olefination/isomerization/Claisen rearrangement (OIC) and reductive cyclization (RC) for construction of the pyrrolo [2,3-b]indole architecture. [15][16][17] Herein we report the first enantioselective total synthesis of (2)-flustramine A (1) and (2)-flustramides A (3) and B (4), along with the second synthesis of (2)-flustramine B (2), following a short and simple approach, which is also diversity oriented.…”

Simple indole alkaloids and those with a non-rearranged monoterpenoid unit

“…101 A total synthesis of (−)-pseudophrynaminol (181), isolated from the skin of the Australian frog Pseudophryne coriacea, 102 has been achieved by a sequence involving 3-allylindol-2-one (182) as a key intermediate (Scheme 35). 103 The enantioselective construction of the quaternary carbon in 182 was performed through a tandem cascade reaction of 2-allyloxyindolin-3one (183), olefination, isomerisation, and asymmetric Claisen rearrangement. Compound 182 was converted into (−)-pseudophrynaminol (181) through the reductive cyclisation of 184.…”