A Fischer Indolization Strategy toward the Total Synthesis of (–)-Goniomitine

Pritchett, Beau P.; Kikuchi, Jun; Numajiri, Yoshitaka; Stoltz, Brian M.

doi:10.3987/com-16-s(s)80

Cited by 14 publications

(2 citation statements)

References 22 publications

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“…Recently, Stoltz et al. employed a palladium‐catalyzed asymmetric allylic alkylation reaction as a key step to install the chiral alkylated quaternary stereocenter in the enantioselective synthesis of 1 ,. Here we report a scalable enantioselective synthesis of (−)‐goniomitine ( 1 ) based on an iridium‐catalyzed asymmetric hydrogenation of racemic 5‐membered exocyclic enone esters.…”

Section: Figuresupporting

confidence: 65%

Scalable Enantioselective Total Synthesis of (−)‐Goniomitine

et al. 2018

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A scalable enantioselective total synthesis of (−)‐goniomitine has been developed by using an iridium‐catalyzed asymmetric hydrogenation of an exocyclic enone ester to control the configuration of the molecule. The synthesis begins from commercially available starting materials, and proceeds through an integrated asymmetric ketone hydrogenation, Johnson–Claisen rearrangement, and one‐pot oxidation/deprotection/cyclization process. With this highly efficient and scalable strategy, (−)‐goniomitine was synthesized in eleven steps with 27 % overall yield, and formal enantioselective syntheses of (+)‐1,2‐dehydroaspidospermidine, (+)‐aspidospermidine, and (+)‐vincadifformine were also achieved.

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Section: Figuresupporting

confidence: 65%

Scalable Enantioselective Total Synthesis of (−)‐Goniomitine

et al. 2018

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“…The scale was compiled by Stoltz [14] and revised by Li Bingquan et al [15], including 4 dimensions of control, ownership, reach and endurance, with a total of 40 items.Likert 5 scoring method is used, the higher the scores show that the higher the adversity quotient. The Cronbach'sα coe cient of this scale was 0.896.…”

Section: College Students' Professional Adaptability Scalementioning

confidence: 99%

The Current Situation and Influencing Factors of Adversity Quotient of Medical Undergraduates

Wang,

Zhou,

et al. 2023

Preprint

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Aims: This study aims to investigate the current situation and related factors of adversity quotient of medical undergraduates. Design: Cross sectional. All participants completed a questionnaire voluntarily and anonymously. Methods: A cross-sectional design was adopted in this study, and medical undergraduates from a university in Lanzhou were selected as convenient samples (n=359). In addition to the socio-demographic questions, the Chinese version of Adversity Response Profile, Professional Identity Questionnaire, college student Professional Adaptability Scale and Coping Style Questionnaire were used to evaluate the characteristics of medical students. Results: The average stress quotient score was 190.91 (SD: 19.74).Multiple linear regression analysis showed that gender (β= -0.119, P=0.015) and professional adaptability (β= 0.379, P＜0.001) were related factors of adversity quotient, which might explain 18.5% of the total variation (F = 12.591, P<0.001). Conclusion: The adversity quotient level of medical undergraduates still has a large space for improvement.Gender and professional adaptability are related factors of adversity quotient. Impact: Adversity quotient is an important ability for medical undergraduates to face setbacks and challenges. Therefore, it is necessary to develop targeted interventions to improve adversity quotient.

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Total Syntheses of rac‐ and (+)‐Goniomitine

Park

Cheon

2019

Adv Synth Catal

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Concise total syntheses of rac-and (+)-goniomitine were developed. The cyanide-catalyzed imino-Stetter reaction of an aldimine, derived from ethyl 2-aminocinnamate and either rac-or (S)α,β-unsaturated aldehyde bearing a δ-valerolactam at the β-position, provided rac-or (S)-indole-3acetate carrying an α-vinyl-δ-valerolactam scaffold at the 2-position, respectively. Subsequent saturation of the vinyl group, followed by treatment with DIBAL-H, afforded N-benzyl protected goniomitine. Final debenzylation provided the desired natural product after only three column separations.

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A Fischer Indolization Strategy toward the Total Synthesis of (–)-Goniomitine

Abstract: A Fischer indolization strategy toward the core of (−)-goniomitine is reported. Initial investigations into the Pd-catalyzed asymmetric allylic alkylation of dihydropyrido[1,2-a]indolone (DHPI) substrates are also discussed.

Cited by 14 publications

References 22 publications

Scalable Enantioselective Total Synthesis of (−)‐Goniomitine

Scalable Enantioselective Total Synthesis of (−)‐Goniomitine

The Current Situation and Influencing Factors of Adversity Quotient of Medical Undergraduates

Total Syntheses of rac‐ and (+)‐Goniomitine

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