Reactive species from aromatics and oxa-di-π-methane rearrangement: a stereoselective synthesis of (±)-hirsutene from salicyl alcohol

Singh, Vishwakarma; Vedantham, P.; Sahu, Pramod K.

doi:10.1016/j.tet.2004.06.096

Cited by 34 publications

(9 citation statements)

References 42 publications

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“…As known, sodium borohydride can reduce conjugated systems to saturated alcohols. 27 The same result was obtained in the reduction of steroid 12: the reaction resulted in the preferential formation of a 17α epimer (according to the NMR data, the 17α/17β ratio was 1.5:1). Under the reaction conditions, removal of the protective group at С3 was also observed.…”

Section: Synthesis Of Steroidal Oxazolessupporting

confidence: 62%

Recent syntheses of steroidal oxazoles, oxazolines and oxazolidines

Bendif¹,

Ibrahim‐Ouali²,

Dumur³

2021

Arkivoc

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Section: Synthesis Of Steroidal Oxazolessupporting

confidence: 62%

Recent syntheses of steroidal oxazoles, oxazolines and oxazolidines

Bendif¹,

Ibrahim‐Ouali²,

Dumur³

2021

Arkivoc

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“…A similar approach by Liao and co-workers was also applied in the synthesis of (±)-Δ 9(12) -capnellene ( 525 ), which was accessed in nine steps with 20% overall yield from 2-methoxy-4-methylphenol ( 524 ) (Scheme ). Additional examples of linear triquinanes that have been assembled utilizing the oxa-di-π-methane rearrangement are (−)-complicatic acid ( 526 ), , (−)-coriolin ( 527 ), − (−)-hirsutene ( 222 ), − (+)-hirsutic acid ( 528 ), ,,, and (−)-phellodonic acid ( 529 ) (Figure ). …”

Section: The Oxa-di-π-methane Rearrangementaccess To Complex Molecul...mentioning

confidence: 99%

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

2016

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The use of photochemical transformations is a powerful strategy that allows for the formation of a high degree of molecular complexity from relatively simple building blocks in a single step. A central feature of all light-promoted transformations is the involvement of electronically excited states, generated upon absorption of photons. This produces transient reactive intermediates and significantly alters the reactivity of a chemical compound. The input of energy provided by light thus offers a means to produce strained and unique target compounds that cannot be assembled using thermal protocols. This review aims at highlighting photochemical transformations as a tool for rapidly accessing structurally and stereochemically diverse scaffolds. Synthetic designs based on photochemical transformations have the potential to afford complex polycyclic carbon skeletons with impressive efficiency, which are of high value in total synthesis.

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“…Two-step sequences involving Diels-Alder reactions and ODPM photoisomerizations were extensively used to build up linear triquinanes scaffolds. [80][81][82][83] As an illustrative example, this type of sequence was successfully involved in the total synthesis of the challenging polycyclic alkaloid megellanine (Scheme 28). 84 Compound 126 was easily obtained by a Diels-Alder reaction between cyclopentadiene and the masked o-benzoquinone 127.…”

Section: Synthetic Application Of Odpm Photoisomerizationmentioning

confidence: 99%