Synthesis of both enantiomers of akolactone B and (+)-ancepsenolide

Hikosaka, Gen; Hattori, Yoshiyuki; Makabe, Hidefumi

doi:10.1016/j.tetasy.2014.08.008

Cited by 12 publications

(2 citation statements)

References 22 publications

(8 reference statements)

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“…21 Several syntheses of 40 have been reported in recent years. 19,22 We envisioned an opportunity to apply our Suzuki-Miyaura coupling protocol for the synthesis of 40. A retrosynthetic perspective for its rapid acquisition employing a α, ω-bis-boronic acid 41 and 3-bromo butenolide 12 was envisaged, Scheme 3.…”

Section: Resultsmentioning

confidence: 99%

A short, general, Suzuki–Miyaura coupling anchored approach to 3-alkenylbutenolides: total synthesis of akolactones A & B, hamabiwalactone B and ancepsenolide

2015

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Section: Resultsmentioning

confidence: 99%

A short, general, Suzuki–Miyaura coupling anchored approach to 3-alkenylbutenolides: total synthesis of akolactones A & B, hamabiwalactone B and ancepsenolide

2015

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“…(+)-Ancepsenolide ( 4 ) represents one of the first butenolide acetogenins, plant metabolites that have shown interesting antitumoral, antimalarial, immunosuppressive, as well as pesticidal activities. Varied biological activity of butanolide and butenolide natural products coupled with structural diversity has attracted significant attention from synthetic chemists, and many of these natural products have succumbed to their total synthesis. − …”

mentioning

confidence: 99%

Donor–Acceptor Substituted Cyclopropane to Butanolide and Butenolide Natural Products: Enantiospecific First Total Synthesis of (+)-Hydroxyancepsenolide

2014

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An oxygen substituted donor-acceptor cyclopropane (DAC) is used as a common intermediate in the enantiospecific collective total synthesis of butanolide- and butenolide-based natural products like (+)-juruenolide C and D, (+)-blastmycinone, (+)-antimycinone, and (+)-ancepsenolide. Enantiospecific first total syntheses of (+)-hydroxyancepsenolide and its acetate are achieved confirming their absolute stereochemistry.

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Hydrozirconation of Alkynes

Milligan,

Hammill,

Crocker

et al. 2023

Organic Reactions

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Since the first preparation of organozirconocenes from alkenes and alkynes in 1972, hydrozirconation has become one of the most commonly used stoichiometric methods to convert readily available starting materials into reactive but stable organometallic intermediates. A broad range of subsequent transformations may be employed to convert organozirconocenes in situ into high‐value functionalized products, often with the strategic formation of one (or several) new carbon–carbon bonds. This chapter focuses on the hydrozirconation of terminal and internal alkynes, and the subsequent synthetic transformations of the resulting alkenylzirconocenes. Zirconocene hydrochloride, Cp 2 Zr(H)Cl, is most frequently employed for the hydrozirconation step and can be used as a reagent or prepared in situ. Subsequent reactions of alkenylzirconocenes include additions to inorganic electrophiles such as halogens, as well as in situ ligand transfers to other metals, such as palladium and zinc, that further expand the range of accessible bond formations. The initial discussion focuses on the mechanism and stereochemical considerations, and on the steric and electronic factors that determine the regiochemistry of the either kinetically or thermodynamically controlled hydrozirconation. The “Scope and Limitations” section presents information on functional group compatibilities and is organized by the type of synthetic transformation of alkenylzirconocenes. Representative applications of the hydrozirconation of alkynes are showcased in syntheses of natural products, comparisons to alternative methods for the hydrometallation of alkynes. The goal of this chapter is to demonstrate the significance of hydrozirconation in organic synthesis, including the utility of the stoichiometric zirconium organometallics obtained from alkyne substrates, and to provide inspiration for the future development of new synthetic methods and strategies.

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Synthesis of both enantiomers of akolactone B and (+)-ancepsenolide

Cited by 12 publications

References 22 publications

A short, general, Suzuki–Miyaura coupling anchored approach to 3-alkenylbutenolides: total synthesis of akolactones A & B, hamabiwalactone B and ancepsenolide

A short, general, Suzuki–Miyaura coupling anchored approach to 3-alkenylbutenolides: total synthesis of akolactones A & B, hamabiwalactone B and ancepsenolide

Donor–Acceptor Substituted Cyclopropane to Butanolide and Butenolide Natural Products: Enantiospecific First Total Synthesis of (+)-Hydroxyancepsenolide

Hydrozirconation of Alkynes

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