First total synthesis of (±)-3-aza-11-oxa-1,3,5(10)-trieno steroids

Oumzil, Khalid; Ibrahim‐Ouali, Malika; Santelli, Maurice

doi:10.1016/j.steroids.2006.06.003

Cited by 21 publications

(9 citation statements)

References 24 publications

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“…The use of the 4-aza-1-mesylbenzocyclobutene 24 32 in the alkylation of spiro lactone 3 gave the corresponding 3aza steroids 25-27 in good yields (Scheme 10). 33,34…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of Unnatural Steroids Using the Bistro Strategy

Maurin

Moraléda

Pellissier

et al. 2015

Synlett

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International audienceLithium-mediated reductive dimerization of buta-1,3-diene in the presence of chloro(trimethyl)silane readily provides 1,8-bis(trimethylsilyl)octa-2,6-diene, commonly known as Bistro'. This bisallylsilane can react with various electrophilic reagents to give 1,1-disubstituted 2,5-divinylcyclopentanes, which are precursors of the D rings of steroids. After slight alterations, these precursors can be coupled with benzocyclobutene derivatives. Heat induces ring opening of the benzocyclobutene to form an o-xylylene that subsequently undergoes intramolecular cycloaddition with a vinyl substituent to form the skeleton of a new unnatural steroid, according to the A + D AD ABCD strategy. In this way, more than 250 steroids have been prepared, including 3-, 11-, 12-heterosteroids bearing a 17-vinyl group that can be readily modified to form a 17-acetyl or 17-(2-oxoethyl) group, as well as some steroid building blocks. The steroids were obtained in few steps from buta-1,3-diene and benzocyclobutene derivatives in overall yields in excess of 25%. This powerful strategy, which has not yet been exhausted, paves the way towards various related synthetic pathways. 1 Introduction 2 Series A 3 Series B 4 Series C 5 Series D 6 Series E 7 X-Ray Crystallographic Data 8 Conclusio

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“…The use of the 4-aza-1-mesylbenzocyclobutene 24 32 in the alkylation of spiro lactone 3 gave the corresponding 3aza steroids 25-27 in good yields (Scheme 10). 33,34…”

Section: Methodsmentioning

confidence: 99%

“…Oxidation of the nitrogen atom of steroid 25, followed by a Wacker-like process, gave the corresponding ketone 28 and aldehyde 29 (Scheme 11). 34…”

Section: Scheme 10mentioning

confidence: 99%

Synthesis of Unnatural Steroids Using the Bistro Strategy

Maurin

Moraléda

Pellissier

et al. 2015

Synlett

Self Cite

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“…Some of them are depicted on Scheme 11 including the access to (±)‐grandifloracin 78 , [105] (−)‐valiolamine 81 , [106] cochlearenine 83 , [107–108] paniculamine 84 , [107–108] pseudo‐β‐fructopyranose 87 , [109] koningic acid derivative 89 , [110] 13α,16α,17‐tri‐hydroxy‐ ent ‐kaur‐19‐oic acid 91 , [111] africane‐9,15‐diol 93 , [112] and trichodermin derivative 95 [113] . Moreover, this strategy has been employed in the synthesis of diverse intermediates which serve as building blocks for further synthesis [114–119] …”

Section: Synthesismentioning

confidence: 99%

Design, Synthesis, and Evaluation of α‐(Hydroxymethyl)cycloalkanols

Nassar

Piva

2021

Eur J Org Chem

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α‐(Hydroxymethyl)cycloalkanols are pervasive structural scaffolds found in natural products and synthetic intermediates with varied biochemical and physicochemical properties. These profiles have driven numerous research groups to the synthesis of such motifs using innovative methodologies. The presence of vicinal diols attached to a cycloalkane makes from these motifs excellent synthetic intermediates for the synthesis of diverse ring systems. This investigation takes an overview of the literature for the occurrence and synthesis of α‐(hydroxymethyl)cycloalkanol derivatives, concentrating on advances in the last two decades.

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“…As a continuation of our synthetic and stereochemical studies on heterocyclic steroidal systems containing two heteroatoms, a similar strategy was used to obtain 3-aza-11-oxa-1,3,5(10)-trieno steroids [132] (Scheme 29).…”

Section: Syntheses Of 3-aza-11-oxasteroidsmentioning

confidence: 99%