Chemoenzymatic access to enantiomeric bicyclo[2.2.1]heptan-2,5-diones

Weissfloch, Alexandra N. E.; Azerad, Robert

doi:10.1016/0968-0896(94)80019-7

Cited by 10 publications

(4 citation statements)

References 16 publications

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“…Norbornadiene was subjected to chiral (bis)hydrosilation (HSiCl 3, (−)- S -MOP, allylpalladium chloride dimer; then H 2 O 2 , KI, KHCO 3 ), which was previously shown to provide the diol corresponding to (+)- 1 with high enantio- and regioselectivity (Scheme ). Swern oxidation gave diketone (+)- 1 , which could be brought to effective enantiomeric purity by simple recrystallization from ether/hexane ([α] D −4.5 ( c 2.7, EtOH), mp 141.5−142 °C). Our attempts to alkylate enolates derived from 1 directly failed due to apparent decomposition.…”

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confidence: 99%

First Asymmetric Total Synthesis of (+)-Sparteine

2002

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confidence: 99%

First Asymmetric Total Synthesis of (+)-Sparteine

2002

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“…The first asymmetric total synthesis of (+)‐sparteine was reported by Aubè in 2002 [24] . The synthetic sequence started from diketone 11 (Scheme 3) which was obtained as a single enantiomer according to a previously reported procedure [25] from norbornadiene. Diketone 11 was firstly monoprotected forming a ketal, then alkylated with BnO(CH 2 ) 3 CHO to give 12 and secondly transformed into azide intermediate 13 .…”

Section: Synthesis Of (−)‐Sparteine and Related Tetracyclic Systemsmentioning

confidence: 99%

Synthesis of Natural Compounds Based on the [3,7]‐Diazabicyclo[3.3.1]nonane (Bispidine) Core

Sacchetti

Rossetti

2021

Eur J Org Chem

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The [3,7]‐diazabicyclo[3.3.1]nonane (bispidine) structure is found in several interesting naturally occurring alkaloids. The most representative components are the tetracyclic alkaloid (−)‐sparteine and the tricyclic (−)‐cytisine alkaloids. Their biological activities have been known for a long time. In the literature, different syntheses of both tetracyclic and tricyclic structures have been reported, especially in the last few years, when a number of new reports renewed the interest in these fascinating molecules. Bicyclic bispidine derivatives have been thoroughly investigated in recent times also for their applications as catalysts, metal chelating agents, and lately in coordination polymers chemistry. In this review, we describe the most relevant strategies for the synthesis of molecules based on the [3,7]‐diazabicyclo[3.3.1]nonane core, related to (−)‐sparteine and (−)‐cytisine alkaloids.

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“…reported an efficient and enantioselective route to hydroxyfuran acetal fragment 77 (Scheme ) 49. The starting point in this approach was chiral alcohol 72 , prepared by kinetic resolution of diketone 71 50 with baker's yeast 51–53. The carbonyl group of 72 was then protected as its O ‐xylidenedioxy acetal and the resulting compound subjected to Swern oxidation conditions.…”

Section: Synthesis Of Azadirachtin Hydroxyfuran Acetal Fragmentsmentioning

confidence: 99%