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- 01HG083GFVGH8185RVERWY6K2G classification C3.
- 01HG083GFVGH8185RVERWY6K2G date "1984".
- 01HG083GFVGH8185RVERWY6K2G language "eng".
- 01HG083GFVGH8185RVERWY6K2G type conference.
- 01HG083GFVGH8185RVERWY6K2G hasPart 01HG08B3YFRBDKSFCYJS54NT8R.pdf.
- 01HG083GFVGH8185RVERWY6K2G subject "Chemistry".
- 01HG083GFVGH8185RVERWY6K2G presentedAt urn:uuid:6a11760b-3314-4353-9a2e-edf1c28c3ff7.
- 01HG083GFVGH8185RVERWY6K2G abstract "Ring annelation reactions, whereby polycyclic molecules are built up, often constitute the core of a synthetis scheme for natural compounds. High stereoselectivity and straightforward introduction of functional groups are essential features of current approaches. We have shown that (2C + 2C)photocycloadditions ar very valuable and superior alternatives to other methods. Thus, photoaddition of 1,2-bis(trimethylsiloxy)cyclopentene to 2-cyclopentenones has proven to be a powerful tool to construct parent skeletons for guaianolides and pseudoguaianolides, i.e. (7,5) ring systems. Even more versatile is the photocoupling of 1,2-bis(trimethylsiloxy)cyclobutene (1) to cyclic enones. This compund serves, via the (2C + 2)photoannelation, as a latent cyclohexa-1,4-dione moiety. Reaction with either 2-cyclopentenones or 2-cyclohexenones produces hydrindanes |(6,5) ring systems| and decalanes |(6,6)ring systems|, respectively. Suitable functionalization then leads to a wide variety of naturally occurring terpenes. In the photoreaction mainly cis-anti-cis regioisomers (2) are formed (quantum yields typically 0.1-0.2). Stereospecific reduction of the carbonyl function, hydrolysis of the silylether groups and oxidative cleavage give rise to the bicyclic compounds 3 and 4 (overall chemical yields between 40 and 60%; up to 1 mole scale). Within the decalanes 4 a predominant trans relationship between R" and OH is observed due to the stereoselectivity in the initial cycloaddition step. Further elaboration of the decalane framework leads to the synthesis of a number of sesquiterpenes such as eudesmanes (e.g. 1-oxocostic acid 5), edesmanolides (e.g. α-santonin 6) and also quaianes (e.g. α-bulnesene 7). Transformation to the tricyclic compound 8 is of key importance for the total synthesis of triterpenes such as labdanes (e.g. marrubiin 9) and nagilactones (e.g. nagilactone F 10). Work towards the use of hydrindane skeleton in the synthesis of natural compounds is in progress.".
- 01HG083GFVGH8185RVERWY6K2G author 6F40B448-B25E-11E6-B104-2D2FD0AF0289.
- 01HG083GFVGH8185RVERWY6K2G author F373969A-F0ED-11E1-A9DE-61C894A0A6B4.
- 01HG083GFVGH8185RVERWY6K2G author urn:uuid:a69e37b7-3000-48e1-a532-e2e84a42b652.
- 01HG083GFVGH8185RVERWY6K2G author urn:uuid:c6dcf77b-ea70-4ccb-9d37-d4e468f5d4d3.
- 01HG083GFVGH8185RVERWY6K2G author urn:uuid:fcf1990d-cb34-4c25-adbd-da37140b078f.
- 01HG083GFVGH8185RVERWY6K2G dateCreated "2023-11-24T08:45:53Z".
- 01HG083GFVGH8185RVERWY6K2G dateModified "2024-11-28T00:09:07Z".
- 01HG083GFVGH8185RVERWY6K2G name "Photoaddition with 1,2-bis(trimethylsiloxy)cyclobutene : a versatile entry to the stereocontrolled total synthesis of various sesqui- and diterpenes".
- 01HG083GFVGH8185RVERWY6K2G pagination urn:uuid:0e219c92-7ac2-4121-9812-3358fb1a4967.
- 01HG083GFVGH8185RVERWY6K2G sameAs LU-01HG083GFVGH8185RVERWY6K2G.
- 01HG083GFVGH8185RVERWY6K2G sourceOrganization urn:uuid:fa2dc3ab-ae8a-45d4-833a-31e5945330ae.
- 01HG083GFVGH8185RVERWY6K2G type C3.