Xyloketals, unique bioactive compounds, isolated from mangrove fungus Xylaria sp. (no. 2508), having multiple pharmacological, therapeutic properties, have prompted enormous research on their stereochemistry, bioactivity and synthetic attempts made toward this novel family. This review brings forward a systematic and comprehensive survey of the method of both racemic and enantioselective synthesis, reactivity, and biological properties associated with the xyloketal derivatives and their analogues.
A step-economic photo-oxidative brominative carbannulation of biaryl ynones employing bromide source and riboflavin tetraacetate (RFTA) have been developed. The switchable reactivity between distal phenyl C-H activatedortho-annulation and dearomative ipso-annulation are well exemplified.The eminent features of the methodology include metal-free, externaladditive free, low-cost photocatalyst, use of simple precursor. Further, we elaborately discussed about the mechanistic investigation and the applicabilityof additional functional group incorporation.
A new one-pot oxidative cleavage of C(sp 2 )À C(sp 3 ) bond has been explored using two complementary protocols employing Phenylselenyl bromide (PhSeBr) as well as Phenyltrimethylammonium Tribromide (PTAB), with much greater efficiency and scope. The oxidative cleavage proceeds via a dearomatization step to afford potentially useful bromonaphthols along with corresponding aldehydes. In this course, we also described the first synthesis of synthetically important azido-halo naphthaleneones.
Bromine induced spiro cyclization of biaryl ynones facilitated the synthesis of spiro [5,5]trienones suitable for extended functionality at the C(3′) position. Herein, a step-economic photo-oxidative brominative carbannulation of biaryl ynones employing ammonium bromide and riboflavin tetraacetate (RFTA) has been developed. The reactivity between distal phenyl C−H activated orthoannulation and dearomative ipso-annulation is well exemplified. The eminent features of the methodology include metal-free, external additive free, low-loading photocatalyst (0.1 mol %), and use of a simple precursor.
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