Total Syntheses of (−)‐Conidiogenone B, (−)‐Conidiogenone, and (−)‐Conidiogenol

Xu, Bo; Xun, Wen; Su, Shaobin; Zhai, Hongbin

doi:10.1002/anie.202007247

Cited by 31 publications

(12 citation statements)

References 57 publications

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“…The second and third syntheses were achieved by the Snyder group (2019) and the Zhai group (2020), respectively. 10,11 Whereas Tu prepared the ABCD tetracyclic skeleton of the cyclopianes via introduction of the B ring onto an ACD spiro-tricycle, the Snyder and Zhai approaches were based on introduction of the A ring onto a pre-existing BCD linear triquinane (Scheme 1); these approaches are outlined in detail.…”

Section: Total Synthesis Of Cyclopiane Diterpenesmentioning

confidence: 99%

“…This approach was notable for the use of the Danheiser annulation to annulate the A ring of the cyclopiane diterpenes (Scheme 8). 11 The Zhai group envisioned that the cyclohexanone moiety (A ring) of 5 could be accessed from 41 via intramolecular aldol reaction with concomitant epimerization of C-5, in which the dicarbonyl functionality of 41 could be introduced via ozonolysis of alkene 42. The tetraquinane skeleton of 42 could be established from triquinane 44 via Danheiser annulation 24,25 with silyl allene 45.…”

Section: Zhai's Asymmetric Total Synthesismentioning

confidence: 99%

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Synthesis of Cyclohexane-Angularly-Fused Triquinanes

Jeon

Winkler

2020

Synthesis

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Cyclohexane-angularly-fused triquinanes, 6-5-5-5 tetracycles, have attracted the attention of synthetic chemists due to their highly congested core structures and multiple quaternary carbon centers. This review focuses on the six completed total synthesis of naturally occurring cyclohexane-angularly-fused triquinanes in addition to seven notable methodologies that have been developed for the synthesis of these structures.1 Introduction2 6-5-5-5 Tetracycles Containing a Linear Triquinane2.1 Total Synthesis of Cyclopiane Diterpenes2.2 Synthetic Approach toward Aberrarane Diterpenes2.3 Intermediates in the Total Synthesis of Magellanine-Type Alkaloids3 6-5-5-5 Tetracycles Containing an Angular Triquinane3.1 Total Synthesis of Waihoensene3.2 Miscellaneous Approaches4 Conclusion

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Section: Total Synthesis Of Cyclopiane Diterpenesmentioning

confidence: 99%

Section: Zhai's Asymmetric Total Synthesismentioning

confidence: 99%

Synthesis of Cyclohexane-Angularly-Fused Triquinanes

Jeon

Winkler

2020

Synthesis

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“…The synthesis of (−)-conidiogenone B ( 171 ) featured a Danheiser’s [3 + 2] annulation [ 74 , 80 ] and was reported by Zhai and co-workers in 2020 [ 73 ] ( Scheme 13 ). Treatment of tricycle 167 with allene 168 in the presence of TiCl 4 gave the desired 169 carrying two vicinal quaternary carbons.…”

Section: Reviewmentioning

confidence: 93%

“…(B) Thiyl-radical-mediated [3 + 2] annulation reaction realizes the synthesis of (−)-pavidolide B (166) [71,72]. (C) A Danheiser's [3 + 2] annulation en route to conidiogenone B (171) [73] (inset, the suggested mechanism based on Danheiser's proposal disclosed in 1981 [74].) its usefulness in forging highly-substituted five-membered carbocycles.…”

Section: All-carbon [3 + 2] Annulation In Natural Product Synthesismentioning

confidence: 99%

All-carbon [3 + 2] cycloaddition in natural product synthesis

Wang¹,

Liu²

2020

Beilstein J. Org. Chem.

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Many natural products possess interesting medicinal properties that arise from their intriguing chemical structures. The highly-substituted carbocycle is one of the most common structural features in many structurally complicated natural products. However, the construction of highly-substituted, stereo-congested, five-membered carbocycles containing all-carbon quaternary center(s) is, at present, a distinct challenge in modern synthetic chemistry, which can be accessed through the all-carbon [3 + 2] cycloaddition. More importantly, the all-carbon [3 + 2] cycloaddition can forge vicinal all-carbon quaternary centers in a single step and has been demonstrated in the synthesis of complex natural products. In this review, we present the development of all-carbon [3 + 2] cycloadditions and illustrate their application in natural product synthesis reported in the last decade covering 2011–2020 (inclusive).

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“…The traditional Barton homolytic scission of C(sp 3 )-O bonds oftentimes requires forcing conditions such as UV irradiation and/or toxic radical inducing reagents, e.g., Bu 3 SnH as radical initiators that add to thionyl-and carbonyl-modified alcohols. 4,5 This conventional strategy has been widely used in the total synthesis of bioactive natural occurring compounds, e.g., (-)-rhodomollanol A, 6 (-)-conidiogenone B, 7 (-)-sculponin R, and (-)-isodocarpin. 8 Recently, a visible-light-induced Barton C-O bond-scission protocol has been developed that allows alkyl (primary, secondary, and tertiary) oxalate salts and tertiary alkyl N-phthalimidoyl (NP) oxalyl esters to generate alkyl radicals under Ir-catalyzed oxidative and Ru-catalyzed reductive conditions, respectively.…”

mentioning

confidence: 99%