Selective preparative ‘oxidase phase’ in sesquiterpenoids: the radical approach

Abstract

The necessity for highly selective oxidative transformations towards the synthesis of complex natural compounds as sesquiterpenoids, renders total synthesis a rich terrain of development for powerful widely applicable methods. Due...

Advancements in the synthesis of polyoxygenated oxepanes and thiepanes for applications to natural products

“…108 The current progression of advancements in the synthesis of oxepanes reveals that new methodologies and opportunities will continue to arise from endeavors in the total synthesis of biologically relevant natural products. While there have been extensive breakthroughs in oxepane synthesis as highlighted in this review, photocatalytic, 210 biocatalytic, and biomimetic strategies 211 that use cascade reactions and incorporate aspects of green chemistry are primed areas for advancement over the next decade to expedite access to complex oxepane natural products.…”

Strategic convergent synthesis en route to Veratrum steroidal alkaloids

“…[9][10][11][12][13] However, assembling the complex skeletons of NPs rapidly remains a daunting challenge in synthetic chemistry. 5,[14][15][16][17][18][19][20][21][22][23][24][25] Over the last decade, semisynthesis has emerged as a powerful tool, enabling the synthesis of many complex NPs, particularly steroids and terpenoids. 26,27 Alternatively, convergent synthesis involves the preparation of multiple functionalized fragments, which are eventually assembled into the precursor and/or the final NPs.…”

Routes to Advanced Intermediates in the Synthesis of Tetracarbocyclic Sesquiterpenoids Daphnenoid A and Artatrovirenols A and B

“…The sesquiterpenes and their oxidized derivatives, the sesquiterpenoids, form a major class of natural products with structures based on 1.5 ( sesqui- ) C 10 -monoterpene units, the first established being those of α-santalol and farnesol . Their wide-ranging biological properties and vast range of structural types have attracted the efforts of synthetic chemists for more than a century, with many of these efforts patterned on biosynthetic speculations . Recently, a new caged-ring sesquiterpenoid subclass has emerged in two papers reporting the structures (Figure ) of artatrovirenols A 1 and B 2 from Artemisia atrovirens , and daphnenoid A 3 from Daphne penicillata .…”

“… 2 Their wide-ranging biological properties and vast range of structural types have attracted the efforts of synthetic chemists for more than a century, with many of these efforts patterned on biosynthetic speculations. 3 Recently, a new caged-ring sesquiterpenoid subclass has emerged in two papers reporting the structures ( Figure 1 ) of artatrovirenols A 1 and B 2 from Artemisia atrovirens , 4 and daphnenoid A 3 from Daphne penicillata . 5 The same tetracyclic ring system is also found in the prenylated phloroglucinol garcinielliptone enantiomers HG and HH from Garcinia subelliptica .…”