In 2012, a group led by Professor Masayuki Satake of the University of Tokyo reported the isolation and structure determination of a toxin from a marine algal bloom that decimated the fish population off the New Zealand coast in 1998. Extensive mass spectrometry and NMR experiments ultimately led to the structure shown below, named Brevisulcenal-F. (See Journal of the American Chemical Society, 2012, 134, 4963–4968.) This structure holds the record for the largest number of fused rings, at 17.
(a) How many ether groups are present?
(b) How many alcohol groups are present? Classify the alcohols as 1° or 2° or 3°.
(c) Are there any other oxygen-containing functional groups? Which, if any?