Enantioselective Biomimetic Cyclization of Homo(polyprenyl)arenes. A New Entry to (+)-Podpcarpa-8,11,13-triene Diterpenoids and (−)-Tetracyclic Polyprenoid of Sedimentary Origin

Ishihara, Kazuaki; Ishibashi, Hiroyuki; Yamamoto, Hisashi

doi:10.1021/ja003541x

Cited by 101 publications

(44 citation statements)

References 22 publications

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“…7 By contrast, enantiose-lective variants of polyene cyclization are less well-developed. 8,9 Since the seminal report by Yamamoto, 9a several methods for enantioselective, proton-initiated polyene cyclizations have been disclosed, but most of these require stoichiometric amounts of chiral Lewis or Brønsted acids. 9a–f and the early catalytic, enantioselective variants require high catalyst loadings.…”

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“…8,9 Since the seminal report by Yamamoto, 9a several methods for enantioselective, proton-initiated polyene cyclizations have been disclosed, but most of these require stoichiometric amounts of chiral Lewis or Brønsted acids. 9a–f and the early catalytic, enantioselective variants require high catalyst loadings. 9g–i In recent years, a few examples of truly catalytic, enantioselective, polyene cyclizations have been reported.…”

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confidence: 99%

“…9a–f and the early catalytic, enantioselective variants require high catalyst loadings. 9g–i In recent years, a few examples of truly catalytic, enantioselective, polyene cyclizations have been reported. In 2017, Yamamoto disclosed an enantioselective bromocycliza-tion of polyenes using a BINOL-derived thiophosphoramide as a chiral Lewis basic catalyst.…”

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Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes

et al. 2018

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A sulfenium-ion-initiated, catalytic, enantio-selective polyene cyclization is described. Homogeranylar-enes and ortho-geranylphenols undergo polycyclization in good yield, diastereoselectivity, and enantioselectivity. The stereodetermining step is the generation of an enantio-merically enriched thiiranium ion from a terminal alkene and a sulfenylating agent in the presence of a chiral Lewis basic catalyst. The use of hexafluoroisopropyl alcohol as the solvent is crucial to obtain good yields. The thioether moiety resulting from the reaction can be subsequently transformed into diverse oxygen and carbon functionality postcyclization. The utility of this method is demonstrated by the enantioselective syntheses of (+)-ferruginol and (+)-hinokiol.

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Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes

et al. 2018

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“…[68][69][70][71] This methodology provided an efficient access to the well-known fragrance ingredient Ambrox ® (20) obtained as an enantioenriched mixture via a triple cyclization of homofarnesol 19 (Scheme 12).…”

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Electrophilic Functionalization of Non-Activated Olefins Catalyzed by Lewis Superacids

Antoniotti¹,

Poulain-Martini²,

Duñach³

2010

Synlett

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“…14 In the present case, 13 provided numerous side products, despite having the stoichiometric cyclizations with (PPP)Pt +2 being selective for a single product. 15 …”

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