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Title: Studies towards the total synthesis and structure elucidation of leiodolide A
Author: Mould, Katy M.
ISNI:       0000 0004 2745 7940
Awarding Body: University of St Andrews
Current Institution: University of St Andrews
Date of Award: 2013
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Leiodolide A is a unique natural product isolated from Pacific marine sponges which has provided an interesting target for total synthesis due to its complex structure and undefined stereochemistry. Although synthetic work towards the synthesis of sister compound leiodolide B has been published, the total synthesis of leiodolide A is yet to be achieved but remains an important target due to high potency against leukaemia, non-small lung and ovarian cancers. The convergent strategy towards the synthesis of leiodolide A involved the synthesis of three subunits; a synthetic route to the C21-C25 vinyl stannane is described, and efforts towards the synthesis of the bidirectional C11-C20 subunit are detailed. Asymmetric vinylogous aldol methodology was developed for the installation of the 1,2-syn propionate motif found in the C1-C10 subunit and in other polypropionate natural products, and was shown to be applicable to a range of substrates in moderate diastereoselectivity and excellent enantioselectivity.
Supervisor: Florence, Gordon John Sponsor: EPSRC-Pharma Synthesis Network ; AstraZeneca
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Natural products ; Total synthesis ; Leiodolide A ; Structural elucidation ; Vinylogous Mukaiyama aldol reaction ; Mixed polyketide non-ribosomal peptide synthetase ; Macrolide ; Polypropionate natural product ; QP752.P65M7 ; Polyketides ; Natural products--Synthesis ; Lactones ; Chemistry ; Organic