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yields (50% vs 28%). The higher yields during ring closure
in the saturated system can be attributed to reduced strain.
Acerogenin C (3) and acerogenin A (2) were synthesized
following reported methods (Scheme 4).4
In summary, we report the first total synthesis of a
strained MDEH natural product ovalifoliolatin B which
was further elaborated to acerogenins C and A.
2. Reddy, V. L. N.; Ravinder, K.; Srinivasulu, M.; Goud, T. V.; Reddy,
S. M.; Srujankumar, D.; Rao, T. P.; Murty, U. S.; Venkateswarlu, Y.
Chem. Pharm. Bull. 2003, 51, 1081–1084.
Acknowledgment
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Financial support from UTMB is gratefully
acknowledged.
Supplementary data
6. (a) Wang, Q.; Son, J. K.; Jahng, Y. Synth. Commun. 2007, 37, 675–
681; (b) Jeong, B. S.; Wang, Q.; Son, J. K.; Jahng, Y. Eur. J. Org.
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7. RCM review on sterically and electronically demanding system: Sieck,
S. R.; Hanson, P. R. Chemtracts 2006, 19, 280–294.
Experimental procedures and complete characterization
of the natural products (1–3) and the intermediates are
available. Supplementary data associated with this article
8. Castedo, L.; Borges, J. E.; Marcos, C. F.; Tojo, G. Synth. Commun.
1995, 25, 1717–1727.
9. See Supplementary data for experimental and analytical data.
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References and notes
1. (a) Ishida, J.; Kozuka, M.; Wang, H.-K.; Konoshima, T.; Tokuda,
H.; Okuda, M.; Yang Mou, X.; Nishino, H.; Sakurai, N.; Lee, K.-H.;